Sodium Carbonate → HCID 59205200, compound

HRID 2242109Notes

Reaction equation

HRID 2242109 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH2:8][OH:9].[C:10]([C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1)#[N:11].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[OH:9][CH2:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[C:16]1[CH:17]=[C:12]([CH:13]=[CH:14][CH:15]=1)[C:10]#[N:11]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 435086(4-bromopyridin-3-yl)methanolHCID 27343253-Cyanophenylboronic acid

Product 1

HCID 59205200HCID 59205200, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a flask charged with (4-bromo-pyridin-3-yl)-methanol (90 mg, 0.48 mmol), 3-cyanophenylboronic acid (84.4 mg, 0.57 mmol) and tetrakis(triphenylphousphine)-palladium(0) (28 mg) was added 2 M Na2CO3 (2 mL) and toluene (3 mL). The reaction mixture was refluxed overnight and then extracted with ethyl acetate. The organic layer was dried over sodium sulfate and purified by column chromatography to yield 3-(3-Hydroxymethyl-pyridin-4-yl)-benzonitrile as a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-6614c1fe0a1f457cb157d842e7ddabe4
Source dataset
uspto-grants-2010_03
Patent number
US07671065B2

Reaction notes

Loading…