Sodium Carbonate → HCID 59205200, compound

HRID 1712069Notes

Reaction equation

HRID 1712069 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-37337f7877814634836ab6cdff4089f8
Source dataset
uspto-grants-2010_09
Patent number
US07790895B2

Reaction notes

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