Sodium Carbonate → HCID 46312076, compound

HRID 860688Notes

Reaction equation

HRID 860688 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-0c2a7cd7b23c4e0c9a509162aa8acadb
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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