Cesium carbonate → HCID 58636873, compound

HRID 1158981Notes

Reaction equation

HRID 1158981 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([OH:11])=[C:5](O)[C:6]([CH3:9])=[N:7][CH:8]=1.Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[N:21])[CH:15]=1.[C:22](=[O:25])([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:20]([C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][O:11][C:4]1[C:3]([CH2:2][OH:1])=[CH:8][N:7]=[C:6]([CH3:9])[C:5]=1[O:25][CH2:22][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[C:20]#[N:21])#[N:21]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 178432807HCID 178432807, compound

Product 1

HCID 58636873HCID 58636873, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-hydroxymethyl-2-methyl-pyridine-3,4-diol (4.0 g, 35.8 mmol), α-bromo-m-tolunitrile (8.8 g, 44.8 mmol) and cesium carbonate (15.6 g, 47.8 mmol) was stirred in DMF (20 mL) for 150 minutes. 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 (1:0 to 19:1) as eluant to give product 3-[4-(3-cyano-benzyloxy)-5-hydroxymethyl-2-methyl-pyridin-3-yloxymethyl]-benzonitrile (161) (2 g, 20% yield).

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 (1:0 to 19:1) as eluant

Sources & evidence

ORD record
ord-37fc19d39d88481f9057fc5c8bfe47ac
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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