3-Bromoaniline → HCID 57517325, compound

HRID 1629714Notes

Reaction equation

HRID 1629714 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9](=O)[CH2:10][CH3:11])=[CH:4][C:3]=1[CH3:13].[Br:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18].[B][B][B][B][B][B][B][B][B][B]>CO>[Br:14][C:15]1[CH:16]=[C:17]([NH:18][CH:9]([C:5]2[CH:6]=[C:7]([CH3:8])[C:2]([Cl:1])=[C:3]([CH3:13])[CH:4]=2)[CH2:10][CH3:11])[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 55269093HCID 55269093, compoundHCID 178419135HCID 178419135, compound

Product 1

HCID 57517325HCID 57517325, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ketone INT 17 (910 mg, 4.63 mmol) and 3-bromoaniline (0.504 mL, 4.63 mmol) in MeOH (25 mL) was added decaborane (283 mg, 2.313 mmol) and the resulting mixture was stirred at room temperature overnight. The mixture was concentrated and purified by chromatography on silica gel (cyclohexane/EtOAc).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by chromatography on silica gel (cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-3bce35da52e447d08f13225dbf677788
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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