N-(4-bromophenyl)-N-methylacetamide → tert-Butyl {4-[[4'-(acetyl-methyl-amino)-4-methoxy-biphenyl-3-ylmethyl]-(3-chloro-benzo[b]thiophene-2-carbonyl)-amino]-cyclohexyl}-methyl-carbamate

HRID 2389595

Reaction equation

HRID 2389595 reaction equation
[C:1]([N:8]([CH3:40])[CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([CH2:28][C:29]2[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][C:34]=2[O:35][CH3:36])[C:16]([C:18]2[S:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[C:19]=2[Cl:27])=[O:17])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:42]1[CH:47]=[CH:46][C:45]([N:48]([CH3:52])[C:49](=[O:51])[CH3:50])=[CH:44][CH:43]=1>>[C:49]([N:48]([CH3:52])[C:45]1[CH:46]=[CH:47][C:42]([C:31]2[CH:32]=[CH:33][C:34]([O:35][CH3:36])=[C:29]([CH2:28][N:15]([C:16]([C:18]3[S:22][C:21]4[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=4[C:19]=3[Cl:27])=[O:17])[CH:12]3[CH2:11][CH2:10][CH:9]([N:8]([CH3:40])[C:1](=[O:2])[O:3][C:4]([CH3:6])([CH3:7])[CH3:5])[CH2:14][CH2:13]3)[CH:30]=2)=[CH:43][CH:44]=1)(=[O:51])[CH3:50]

Participants

3

Reactant 2

HCID 4324567N-(4-bromophenyl)-N-methylacetamideHCID 596836463-{[[4-(BOC-methyl-amino)-cyclohexyl]-(3-chlorobenzo[b]thiophene-2-carbonyl)-amino]-methyl}-4-methoxy-benzene boronic acid

Product 1

HCID 59683645tert-Butyl {4-[[4'-(acetyl-methyl-amino)-4-methoxy-biphenyl-3-ylmethyl]-(3-chloro-benzo[b]thiophene-2-carbonyl)-amino]-cyclohexyl}-methyl-carbamate

Procedure

Boronic acid 5 (200 mg, 0.34 mmol) is coupled to aryl bromide 62 (93 mg, 0.41 mmol) using Method B to give the title compound.

Sources & evidence

ORD record
ord-284e75d149ab4d2a884ac27444ed569d
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Linked notes

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