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Acetic Anhydride 139, 173, 192, 195, 196, 204

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Acetic Anhydride 139, 173, 192, 195, 196, 204 j357 Index a 2-amino-3-methylpyridine 40 acetic anhydride 139, 173, 192, 195, 196, 204 4-aminopyridine 329, 330 acetonedicarboxylate 41 2-aminotetralin, chiral 73 acid, as metal chelator 274 aminotetralin, racemic 74 acrylate, as by-product 255 ammonia acyl azide 234 – in Buchwald–Hartwig amination 304 adapalene 322 – to solubilize magnesium salts 274 adiabatic cooling 283 amphiphiles 300 aldehyde 5, 234 angiotensin 1-converting enzyme inhibitor 1 alkoxycarbonylation 288 angiotensin II receptor antagonist 21 – ethoxycarbonylation 290 aniline 2 O-allylation 190 o-anisidine 202 allyl bromide 26, 190 antibiotic allyl t-butyl carbonate 191 – cethromycin 189, 190 p-allyl complex, from allyl carbonate 190 – daptomycin 91 allylic alcohol 195 – EDP-420 189, 192, 195 4-allylisoindoline 267 – erythromycin A 189 allylmagnesium chloride 269, 273 – Ketek 189 – as base 272 – ketolide 189 p-allylpalladium complex 189–191, 193 – linezolid 91 alumina plug 336 – macrolide 189 amidase 5 – quinoline pyrimidine trione 91 amidation, metal-catalyzed – telithromycin 189 – base particle size effect 229 anti-elimination, base-induced 53 – copper-catalyzed 225 antimitotic agent 343 – of enol triflate 225 N-arylalkyl group, as hydride donor 79 – palladium-catalyzed 223, 225 O-arylation 207, 208 – water effect 229 aryl group exchange 172, 258 amide condensation 42, 74, 217, 218 aryllithium 254 a-amino acid 4 atom economy 239 amino acid arylation axitinib 165, 345 – copper-catalyzed 8 azadipeptide 323 – palladium-catalyzed 8 azepane 239 amino acid dehydrogenase 5 azepanone 233 amino acid synthesis, enzymatic 8 azlactone 5 amino acid, unnatural 5 2-amino-1,3-benzothiazol-4-ol 202 b aminocarbonylation 291 barbituric acid 101 1-aminocyclobutanecarboxylic acid 105 Bayesian reliability approach 242 Transition Metal-Catalyzed Couplings in Process Chemistry: Case Studies from the Pharmaceutical Industry, First Edition. Edited by Javier Magano and Joshua R. Dunetz Ó 2013 Wiley-VCH Verlag GmbH & Co. KGaA. Published 2013 by Wiley-VCH Verlag GmbH & Co. KGaA. 358j Index 9-BBN 28 Bu2BOTf 123 benign by design 300, 308 Bucherer–Bergs reaction 5 3-benzonitriles 217 Buchwald–Hartwig amination 8, 16, 74, 76, benzophenone 330 139, 304, 309, 314, 318, 330, 331, 333, 338 benzophenone hydrazone 314 butyl acrylate 282 benzophenone imine 330, 331 t-butylamine 68 benzylamine 75 t-butyl carbamate of ammonia, in benzyloxy carbamate of ammonia Buchwald–Hartwig amination 304 – in Buchwald–Hartwig amination 304 i-butyl chloroformate 52 benzyltriethylammonium bromide tert-butylimino-tri(pyrrolidino) – additive for Negishi coupling 110 phosphorane 235, 245 Á BF3 2AcOH 30 tert-butyl nitrite 234 BH3ÁTHF 31 N-t-butylpiperidine 40 bicyclolide 199 butyl vinyl ether 344 2,20-bipyridine 110 3-butyn-1-ol 336 bis-p-allylation 192–199 3-butyn-2-ol 326 – stepwise 194 – tandem inter- and intramolecular 192 c bisboron reagent 27 cannabinoid-1 receptor inverse agonist 217 1,8-bis(dimethylamino)naphthalene 168 carbamate 237 bis(pinacolato)diboron 96 carbon acid bisulfite adduct, for aldehyde purification 93 – malonate 30 Boc-piperazine 333 – in Pd-catalyzed coupling 30, 31 borane, in situ generation 35 carbon footprint 10 boraneÁMe3N 347 carbon monoxide, in carbonylation borate complex 107, 317, 332 reaction 287 boronate ester 97, 100 carbonylation boron scavenger, ethanolamine 29 – under continuous-flow processing 291 boroxine 128 – under microwave heating 287 – effect on Rh-catalyzed asymmetric Michael – palladium-catalyzed 287 reaction of boronic acid 132 catalyst activation 74, 83, 129 borylation 108, 109 catalyst deactivation 234 – Miyaura borylation 91, 95 – by peroxide in THF 132 2-borylsilane 27, 28 catalyst inhibition B-Raf kinase inhibitor 16, 343 – by ligand 173 bromine migration 87 – palladium, by cyanide 222 4-bromoanisole 284, 285, 286, 304 catalyst loading 4-bromobenzaldehyde dimethyl acetal 21 – effect on residual metal content 314 3-bromobenzonitrile 217 catalyst recycling 160, 314 1-bromo-4-chlorobenzene 324 catalyst resting state 153 4-bromo-2-chloro-3-iodopyridine 47 cathepsin K inhibitor 233, 325 4-bromo-1-chloroisoquinoline 16 cathepsin S inhibitor 57 1-bromo-3-chloropropane 59 – peptide 57 5-bromo-2,4-difluorobenzaldehyde 93 CDI 62 5-bromo-2-hydroxynicotinic acid 25 chelation, to heavy metals 143 bromoindole 316 chiral auxiliary 4-bromoisoindoline 267 – ephedrine-based 123 2-bromo-5-methyl-1,3,4-thiadiazole 97, 100 – oxazolidinone 234 bromonaphthalene 322 chiral metal complex 121 3-bromophenyl acetic acid 217 chlorination 101 2-bromopyridine 105, 323, 330 2-chloro-3-aminopyridine 25 N-bromosuccinimide 93 4-chlorobenzylamine 59 bromotetralin 74 4-chlorobenzyl bromide 217 Index j359 4-chlorobenzyl chloride 218 decarboxylation 30 4-chloro-N-t-butylpiperidine 41, 49 dechlorination 40 a-chlorocarboxylic acid 2 degassing 219, 221 4-chloro-3-iodopyridine 47 – to reduce residual palladium 314 2-chloro-5-iodopyrimidine 322 dehydroalanine 5 m-chloroperoxybenzoic acid 50 design of experiments 139, 247 N-chlorosuccinimide 101 Dess–Martin reagent 57 cholecystokinin 1R receptor agonist 333 desymmetrization 235 chromatography 237, 315 2D heteronuclear multiple-bond – on c-alumina 341 correlation 45 – on silica 183 diarylborinic acid 318 cinnamic acid 5 diaryl ether 328, 341 citric acid, to solubilize magnesium salts 274 diaryl ether formation 202, 207 cladinose 195, 196, 198 – copper-catalyzed 315 classical resolution 1, 74 diastereomer equilibration 101 c-Met/ALK inhibitor 340 DIBAL-H 324 c-Met kinase inhibitor 332 dibenzylamine 68 cocrystal 66 dibromantin 93 continuous-flow processing 280 1,3-dibromo-5,5-dimethylhydantoin 93 copper catalyst/precatalyst di-t-butyl dicarbonate 147 – copper bronze 330 2,6-dichloroaniline 43 – CuBr 140 2,6-dichlorophenylacrylamide 47 – CuBr2 140 4,6-dichloropyrimidine 202, 205 – CuCl 9, 341 diene 234, 235, 239 – CuI 6, 27, 58, 63, 107, 137, 140, 142, 181, 182, diethyl malonate 31 185, 327, 328, 331, 337, 339, 347 diethyl oxalate 66 – CuO 140 Differin 322 – Cu2O 6, 321 2,4-difluorobenzaldehyde 93 – Cu(OAc)2 140, 308 difluoromethylation 182 corticotropin-releasing factor antagonist 2,4-difluorophenylboronic acid 43, 48 328, 346 3,5-difluorophenylboronic acid 127 COX-II selective inhibitor 341 1,2-dihalobenzene, in Heck coupling 5 CRF-1 antagonist 136 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine 136 critical micelle concentration 299 dimethyl carbonate, as solvent in RCM 239 crizotinib 340 (R,R)-2,6-dimethylmorpholine 93, 94 cross-metathesis 303 diphenyl pyrrolidine-2-phosphonate 6 crotonate imide 234 di(2-pyridyl)zinc 112 Curtius rearrangement 234, 237 directed metalation 26 cyanation (þ)-discodermolide 317 – palladium-catalyzed 219–224, 323, 338 distillation, for aldehyde purification 93 – water effect 221 disulfide 254 cyanide, additive effect on solubility 222 divinyl carbinol 235 cyanide scavenger, ammonium diyne 185 hydroxide 221 D-proline 2 cyanohydrin 32 dynamic kinetic resolution 217, 222, 223 cyclization 25 dynamic light scattering 301 – copper-catalyzed 1, 6, 8 cyclopropanation 331 e ebalzotan 73 d Eco-indicator 99 10 DBU 141, 208, 244 E-factor 86 – D3/D2/5-HT2 receptor antagonist 335 enamide 5, 223 229 debenzylation 74 enolate 42, 122 360j Index – a-arylation, palladium-catalyzed 30–36, 324 glycolic acid, to solubilize magnesium enolization salts 274 – of NMP with organozinc reagent 113 Goldberg amidation 135 enol sulfonate 223 gold trichloride enol triflate – catalyst in Michael reaction 307 – isomerization 225 gradient-enhanced nuclear Overhauser enzymatic resolution 1 effect 45 EP1 antagonist 318 green chemistry 1, 85 epimerization 5 – twelve principles 300 epoxide 235, 243 Grignard reagent 21, 26, 40, 49, 112, 123, 254, Erlenmeyer reaction 5 267, 322, 323, 324 erythromycin A 9-oxime 190, 192, 195, 196 – i-PrMgCl 26, 49, 112 etching, by hydroxyde 34 – vinylmagnesium chloride 147 ethyl acetate, to quench NMP enolate 115 ethylamine 25 h ethyl p-aminocinnamate 105 HATU 57, 62 ethyl benzoate 290 HCV NS5B polymerase inhibitor 105 ethyl 2-bromo-2,2-difluoroacetate 330 Hayashi–Miyaura coupling 121, 122, 133 ethyl carbamate of ammonia, in – water effect 132 Buchwald–Hartwig amination 304 Heck coupling 5, 26, 47, 147, 165, 168, 173, ethylene 249 192, 267, 302, 314, 344, 345 – release during RCM 241 – carbopalladation step 151 ethylene carbonate – catalytic cycle 150 – as solvent 48 – double arylation product 155 ethyl 3-ethoxyacrylate 43 – intramolecular 320 ethylhexyl acrylate 255 – large vessel approach under microwave N-ethyl-4-piperidone 40 heating 284 ethyne surrogate 343 – mechanism 152 ethynylbenzaldehyde 59 – with microwave heating 281 4-ethynylbenzaldehyde 59 – open-vessel approach using MW heating 281 2-ethynylpyridine 182, 183, 185 – oxygen effect 158 Et2Zn 220, 221, 224 – regioisomer formation 147 Evans aldol condensation 234 – semi-continuous process 161 – solvent-free using MW heating 281 f – stereoisomer formation 147 fenleuton 326, 331 – stop-flow approach using MW heating 283 filter aid – water effect 157 – Celite 36 Heck coupling-lactamization 48 – Cellflock 317 Heck-lactamization 42, 47 – Harbolite clay 314 hemiketal 192, 193 – Hyflo super cel 323 hepatitis C virus protease inhibitor 326 – Solka-Floc 332 – NS3/4a protease inhibitor 267 – Solka-Floc 40 NF 329 heterocycle, N-arylation 137 Fisher indole synthesis 1 heterogeneous catalyst 314 Florisil 166 heterogeneous mixtures, in flow fools gold 348 processes 280 formaldehyde 325 hexamethyldistannane 40 Friedel–Crafts reaction 87 n-HexLi, as alternative to n-BuLi 19 fungicidal derivative 324 high-pressure equipment
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