2,4-Difluorophenylboronic acid → (2S)-2-{(S)-[(2', 4'-difluorobiphenyl-4-yl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid (1-cyanocyclopropyl)-amide

HRID 1009310Notes

Reaction equation

HRID 1009310 reaction equation
[C:1]([C:3]1([NH:6][C:7](=[O:27])[C@@H:8]([NH:13][C@@H:14]([C:20]2[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=2)[C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][CH2:4]1)#[N:2].[F:28][C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=1B(O)O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([C:3]1([NH:6][C:7](=[O:27])[C@@H:8]([NH:13][C@@H:14]([C:20]2[CH:25]=[CH:24][C:23]([C:32]3[CH:31]=[CH:30][C:29]([F:28])=[CH:34][C:33]=3[F:35])=[CH:22][CH:21]=2)[C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 27343342,4-Difluorophenylboronic acidHCID 67298346(2S)2-{(S)-[(4-bromophenyl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid (1-cyanocyclopropyl)-amide

Product 1

HCID 59715509(2S)-2-{(S)-[(2', 4'-difluorobiphenyl-4-yl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid (1-cyanocyclopropyl)-amide

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

The title compound was prepared via the Suzuki cross-coupling of (2S)-2-{(S)-[(4-bromophenyl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid (1-cyanocyclopropyl)-amide with 2,4-difluorobenzeneboronic acid, in the presence of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), dichloromethane complex. MS (−ESI): 479 [M−1]−

Sources & evidence

ORD record
ord-da434fb1d52c444aab6ff8f12a87ba79
Source dataset
uspto-grants-2011_07
Patent number
US07973037B2

Reaction notes

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