1-Bromo-4-((methylsulfonyl)methyl)benzene → tert-Butyl{4-[(4'-methanesulfonylmethyl-4-methoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

HRID 2389663Notes

Reaction equation

HRID 2389663 reaction equation
[C:1]([N:8]([CH3:28])[CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][CH2:16][C:17]2[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:30]1[CH:35]=[CH:34][C:33]([CH2:36][S:37]([CH3:40])(=[O:39])=[O:38])=[CH:32][CH:31]=1>>[CH3:40][S:37]([CH2:36][C:33]1[CH:34]=[CH:35][C:30]([C:19]2[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:17]([CH2:16][NH:15][CH:12]3[CH2:13][CH2:14][CH:9]([N:8]([CH3:28])[C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH2:10][CH2:11]3)[CH:18]=2)=[CH:31][CH:32]=1)(=[O:38])=[O:39]

Participants

3

Reactant 2

HCID 27614151-Bromo-4-((methylsulfonyl)methyl)benzeneHCID 252081913-{[4-(BOC-methyl-amino)-cyclohexylamino]-methyl}-4-methoxy-benzene boronic acid

Product 1

HCID 59683471tert-Butyl{4-[(4'-methanesulfonylmethyl-4-methoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

Procedure

Boronic acid 4 (200 mg, 0.51 mmol) is coupled to aryl bromide 197 (127 mg, 0.51 mmol) using Method A. On filtration of the cooled reaction mixture through celite and removal of the solvents in vacuo, the crude residue obtained is used in the next synthetic step without further purification.

Workup

  1. filtrationOn filtration of the cooled reaction mixture
  2. customthrough celite and removal of the solvents in vacuo

Sources & evidence

ORD record
ord-1d10fab51f554a0c97d1b6b2915508bc
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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