Sodium Carbonate → HCID 69130419, compound

HRID 915646Notes

Reaction equation

HRID 915646 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8](Br)=[CH:9][CH:10]=1)=[O:4].[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[C:15]([CH3:22])[CH:14]=1.[F-].[Cs+].C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:8]2[N:7]=[CH:6][C:5]([C:3]([OH:2])=[O:4])=[CH:10][CH:9]=2)=[C:15]([CH3:22])[CH:14]=1

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 25953Cesium fluorideHCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 13349623Methyl 6-bromopyridine-3-carboxylate

Product 1

HCID 69130419HCID 69130419, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Combine 6-bromopyridine-3-carboxylic acid methyl ester (387 mg, 1.79 mmol), 4-fluoro-2-methylphenylboronic acid (338 mg, 2.19 mmol), Pd(OAc)2 (40 mg, 0.18 mmol), cesium fluoride (27 mg, 0.18 mmol) and sodium carbonate (570 mg, 5.38 mmol) in dimethylformamide (6 mL) and water (6 mL) with stirring. Purge the reaction mixture with N2, add triphenylphosphine (47 mg, 0.18 mmol), and purge again with N2. Place the sealed reaction in an oil bath maintained at 80° C. and allow to stir for 17 hours. Cool the reaction to room temperature and pass through a short plug of silica gel. Wash the column with dichloromethane (100 mL) followed by aqueous methanol (100 mL, 3 methanol/1 water). Reduce the combined fractions in vacuo and suspend the residual solid in water (10 mL). Filter to remove a black solid and acidify with 1N hydrochloric acid solution to pH 4. A white precipitate forms which is collected by filtration and dried to give 306 mg (74%) of the title compound. MS (m/e): 231.9 (MH+).

Workup

  1. customPurge the reaction mixture with N2
  2. custompurge again with N2
  3. customthe sealed reaction in an oil bath
  4. temperatureCool
  5. customthe reaction to room temperature
  6. washWash the column with dichloromethane (100 mL)
  7. filtrationFilter
  8. customto remove a black solid
  9. filtrationA white precipitate forms which is collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-2ce0fe36b10d4c0aa5f03c3fc5308689
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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