2-Bromophenylacetyl chloride → 5-[2-(2-Bromo-phenyl)-acetylamino]-4'-methyl-biphenyl-3-carboxylic acid methyl ester

HRID 2406896Notes

Reaction equation

HRID 2406896 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:8]=[C:9]([NH2:11])[CH:10]=1)=[O:4].[Br:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][C:27](Cl)=[O:28]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:8]=[C:9]([NH:11][C:27](=[O:28])[CH2:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[Br:19])[CH:10]=1)=[O:4]

Participants

5

Reactant 2

HCID 41383862-Bromophenylacetyl chlorideHCID 57850917Methyl 5-amino-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 596277535-[2-(2-Bromo-phenyl)-acetylamino]-4'-methyl-biphenyl-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 5-amino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (241 mg, 1.0 mmol), pyridine (0.5 mL), DMAP (10 mg) and 2-bromophenylacetyl chloride (253 mg, 1.1 equiv.) was stirred for one hour at room temperature. The mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, and the organic layer was separated and concentrated under reduced pressure to give crude 5-[2-(2-bromo-phenyl)-acetylamino]-4′-methyl-biphenyl-3-carboxylic acid methyl ester, which was used directly in the next step.

Workup

  1. customThe mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. customthe organic layer was separated
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c72b609296b46d78a4a3601e394955e
Source dataset
uspto-grants-2014_08
Patent number
US08809402B2

Reaction notes

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