4-Bromopyridinium chloride → tert-Butyl {4-[(3-chloro-4,7-difluoro-benzo[b]thiophene-2-carbonyl)-(2-methoxy-5-pyridin-4-yl-benzyl)-amino]-cyclohexyl}-methyl-carbamate

HRID 2389629Notes

Reaction equation

HRID 2389629 reaction equation
[C:1]([N:8]([CH3:42])[CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([CH2:30][C:31]2[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[C:16]([C:18]2[S:22][C:21]3[C:23]([F:28])=[CH:24][CH:25]=[C:26]([F:27])[C:20]=3[C:19]=2[Cl:29])=[O:17])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.Br[C:45]1[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=1>>[Cl:29][C:19]1[C:20]2[C:26]([F:27])=[CH:25][CH:24]=[C:23]([F:28])[C:21]=2[S:22][C:18]=1[C:16]([N:15]([CH2:30][C:31]1[CH:32]=[C:33]([C:45]2[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=2)[CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[CH:12]1[CH2:11][CH2:10][CH:9]([N:8]([CH3:42])[C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:7])[CH3:6])[CH2:14][CH2:13]1)=[O:17]

Participants

3

Reactant 2

HCID 881004-Bromopyridinium chlorideHCID 596835093-{[[4-(BOC-methyl-amino)-cyclohexyl]-(3-chloro-4,7-difluoro-benzo[b]thiophene-2-carbonyl)-amino]-methyl}-4-methoxy-benzene boronic acid

Product 1

HCID 59683496tert-Butyl {4-[(3-chloro-4,7-difluoro-benzo[b]thiophene-2-carbonyl)-(2-methoxy-5-pyridin-4-yl-benzyl)-amino]-cyclohexyl}-methyl-carbamate

Procedure

Boronic acid 9 (5.70 g, 9.14 mmol) is coupled to 4-bromopyridine hydrochloride (2.13 g, 11.0 mmol) using Method A to give the title compound.

Sources & evidence

ORD record
ord-1babb81bf0064ff0b70583ebf9861905
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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