Sodium Carbonate → HCID 46312076, compound

HRID 854573Notes

Reaction equation

HRID 854573 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 46312076HCID 46312076, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-Chloro-nicotinonitrile (7.26 g, 52.4 mmol) and 2-fluorophenyl boronic acid (11 g, 78.6 mmol) and Na2CO3 (11 g, 103 mmol) in toluene (200 mL) and water (10 mL) is degassed and filled with nitrogen for three times, then Pd(PPh3)4 (0.73 g) is added under nitrogen. The reaction mixture is heated at 90° C. After 12 hrs, the reaction mixture is cooled to room temperature, diluted with ethyl acetate, washed with water, dried, concentrated. Column chromatography on silica gel (Hexane/ethyl acetate as eluent) gave 9.8 g of 6-(2-Fluoro-phenyl)-nicotinonitrile.

Workup

  1. customis degassed
  2. additionfilled with nitrogen for three times
  3. additionPd(PPh3)4 (0.73 g) is added under nitrogen
  4. temperaturethe reaction mixture is cooled to room temperature
  5. additiondiluted with ethyl acetate
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-281d4c7d35db42c7bed0a796257eb280
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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