Potassium Carbonate → HCID 68644152, compound

HRID 1158930Notes

Reaction equation

HRID 1158930 reaction equation
[OH:1][C:2]1[C:3]([CH3:20])=[N:4][CH:5]=[C:6]([CH2:18][OH:19])[C:7]=1[CH2:8][NH:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([CH2:22][O:1][C:2]2[C:3]([CH3:20])=[N:4][CH:5]=[C:6]([CH2:18][OH:19])[C:7]=2[CH2:8][NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[CH:24][CH:25]=1)#[N:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 59513912HCID 59513912, compound

Product 1

HCID 68644152HCID 68644152, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[(3-hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-ylmethyl)-amino]-benzonitrile (1)* (404 mg, 1.5 mmol), α-bromo-p-tolunitrile (322 mg, 1.65 mmol), potassium carbonate (622 mg, 4.5 mmol) and DMF (10 mL) was stirred at room temperature under nitrogen atmosphere overnight. The reaction mixture was evaporated to dryness, and the crude product purified by column chromatography on silica gel using a gradient of dichloromethane:methyl alcohol (9:1) as eluant to give 4-{[3-(3-cyano-benzyloxy)-5-hydroxymethyl-2-methyl-pyridin-4-ylmethyl]-amino}-benzonitrile (2) (348 mg, 60% yield) as a colorless solid.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe crude product purified by column chromatography on silica gel using a gradient of dichloromethane:methyl alcohol (9:1) as eluant

Sources & evidence

ORD record
ord-158782dccae84ca0b7f96950b6e22ef2
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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