4'-Bromo-2,2,2-trifluoroacetophenone → tert-Butyl (4-{[4-methoxy-4'-(2,2,2-trifluoro-acetyl)-biphenyl-3-ylmethyl]-amino}-cyclohexyl)-methyl-carbamate

HRID 2389570Notes

Reaction equation

HRID 2389570 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]([C:36](=[O:41])[C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=1>>[CH3:24][O:23][C:22]1[CH:21]=[CH:20][C:19]([C:30]2[CH:35]=[CH:34][C:33]([C:36](=[O:41])[C:37]([F:39])([F:40])[F:38])=[CH:32][CH:31]=2)=[CH:18][C:17]=1[CH2:16][NH:15][CH:12]1[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]1

Participants

3

Reactant 2

HCID 6038664'-Bromo-2,2,2-trifluoroacetophenoneHCID 252081913-{[4-(BOC-methyl-amino)-cyclohexylamino]-methyl}-4-methoxy-benzene boronic acid

Product 1

HCID 59683508tert-Butyl (4-{[4-methoxy-4'-(2,2,2-trifluoro-acetyl)-biphenyl-3-ylmethyl]-amino}-cyclohexyl)-methyl-carbamate

Procedure

Boronic acid 4 (620 mg, 1.60 mmol) is coupled to 4′-bromo-2,2,2-trifluoroacetophenone (400 mg, 1.60 mmol) using Method B to give the title compound.

Sources & evidence

ORD record
ord-7534c71d45304f898aa5df910b513886
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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