4-Bromobenzyl alcohol → tert-Butyl {4-[(3-chloro-benzo[b]thiophene-2-carbonyl)-(4'-hydroxymethyl-4-methoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

HRID 2389610Notes

Reaction equation

HRID 2389610 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]([CH2:48][OH:49])=[CH:44][CH:43]=1>>[Cl:27][C:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[S:22][C:18]=1[C:16]([N:15]([CH2:28][C:29]1[CH:30]=[C:31]([C:42]2[CH:47]=[CH:46][C:45]([CH2:48][OH:49])=[CH:44][CH:43]=2)[CH:32]=[CH:33][C:34]=1[O:35][CH3:36])[CH:12]1[CH2:11][CH2:10][CH:9]([N:8]([CH3:40])[C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:5])[CH3:6])[CH2:14][CH2:13]1)=[O:17]

Participants

3

Reactant 2

HCID 701194-Bromobenzyl alcoholHCID 596836463-{[[4-(BOC-methyl-amino)-cyclohexyl]-(3-chlorobenzo[b]thiophene-2-carbonyl)-amino]-methyl}-4-methoxy-benzene boronic acid

Product 1

HCID 59683467tert-Butyl {4-[(3-chloro-benzo[b]thiophene-2-carbonyl)-(4'-hydroxymethyl-4-methoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

Procedure

Boronic acid 5 (210 mg, 0.36 mmol) is coupled to (4-bromophenyl)-methanol (80 mg, 0.43 mmol) using Method B to give the title compound.

Sources & evidence

ORD record
ord-77ac3fb42c76494b9391549df3806cf2
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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