Water → 4-Bromo-2-(methylamino-pyridin-2-yl-methyl)-phenylamine

HRID 1497727

Reaction equation

HRID 1497727 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=O.[CH3:17][NH2:18].[BH4-].[Na+].O>CO>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([CH:9]([NH:18][CH3:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 738072-(2-Amino-5-bromobenzoyl)pyridineHCID 4311764Sodium borohydride

Product 1

HCID 1176000614-Bromo-2-(methylamino-pyridin-2-yl-methyl)-phenylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2-Amino-5-bromo-phenyl)-pyridin-2-yl-methanone (500 mg, 1.8 mmol) in MeOH (20 mL) is added Ti(i-OPr)4 (1.0 g, 3.6 mmol) and methylamine (2M in THF, 4.5 mL). Then the mixture is stirred at room temperature for 6 h. Sodium borohydride (137 mg, 3.6 mmol) is added in one portion. The mixture is stirred at room temperature for 2 h. Water (10 mL) is added and the mixture is filtered and washed with EtOAc. The filtrate is washed with brine, the organic layer is concentrated in vacuum to give the desired product as a crude mixture. This is used in next step with no further purification.

Workup

  1. stirringThe mixture is stirred at room temperature for 2 h
  2. filtrationthe mixture is filtered
  3. washwashed with EtOAc
  4. washThe filtrate is washed with brine
  5. concentrationthe organic layer is concentrated in vacuum

Sources & evidence

ORD record
ord-f78acaec11814ce090ccbb08b374793c
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Linked notes

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