Water → HCID 9930360, compound

HRID 2300189Notes

Reaction equation

HRID 2300189 reaction equation
Br[C:2]1[C:3]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[N:4][N:5]2[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:6]=12.[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(=[O:23])=[O:22].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:3]2[C:2]([C:27]3[CH:28]=[CH:29][C:24]([S:21]([CH3:20])(=[O:23])=[O:22])=[CH:25][CH:26]=3)=[C:6]3[CH:7]=[CH:8][C:9]([C:11]#[N:12])=[CH:10][N:5]3[N:4]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 18376033HCID 18376033, compound

Product 1

HCID 9930360HCID 9930360, compoundYield 6.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-6-carbonitrile (0.24 g 0.76 mmol) in DMF (20 ml) was added 4-methanesulfonylphenylboronic acid (0.202 g 1.1 mmol), ground potassium phosphate (0.45 g 20 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.03 g) and the mixture heated to 90° for 6 h under nitrogen. The cooled mixture was poured into water (200 ml) and extracted with ethyl acetate (3×40 ml). The combined organic phases were washed with water (50 ml), brine (50 ml) and dried. Removal of solvent gave a solid which was purified by biotage chromatography. Elution with cyclohexane:ethyl acetate (4:1) gave the title compound as a white solid (0.019 g 6%). MH+: 392; NMR: (CDCl3) δ 3.14 (3H, s) 7.09 (2H, t) 7.30 (1H, dd) 7.50-7.56 (4H, m) 7.62 (1H, dd) 8.00 (2H, d) 8.9 (1H, s).

Workup

  1. temperaturethe mixture heated to 90° for 6 h under nitrogen
  2. extractionextracted with ethyl acetate (3×40 ml)
  3. washThe combined organic phases were washed with water (50 ml), brine (50 ml)
  4. customdried
  5. customRemoval of solvent
  6. customgave a solid which
  7. customwas purified by biotage chromatography
  8. washElution with cyclohexane:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-b2c37708fabb40f1b28fd01b3b38a9bf
Source dataset
uspto-grants-2002_12
Patent number
US06498166B1

Reaction notes

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