Water → HCID 9954593, compound

HRID 1354174Notes

Reaction equation

HRID 1354174 reaction equation
Br[C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[N:4][N:5]2[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=12.[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)(=[O:25])=[O:24].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:21][C:17]1[CH:16]=[C:15]([C:3]2[C:2]([C:29]3[CH:30]=[CH:31][C:26]([S:23]([CH3:22])(=[O:25])=[O:24])=[CH:27][CH:28]=3)=[C:6]3[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][N:5]3[N:4]=2)[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 11772769HCID 11772769, compound

Product 1

HCID 9954593HCID 9954593, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of the 3-bromo-2-(3-fluoro-phenyl)-6-trifluoromethyl-pyrazolo[1,5-a]pyridine (50 mg, 0.139 mmol) in DMF (5 ml) was added 4-methanesulfonylphenylboronic acid (37 mg, 1.3 eq), ground potassium phosphate (83 mg) and tetrakis(triphenylphosphine)palladium(0) (10 mg) and the mixture heated to 90° for 18 h under N2. The cooled mixture was poured into water (10 ml) and extracted into ethyl acetate (4×10 ml). The combined organic phases were washed sequentially with water, brine, 2N sodium hydroxide and brine, dried and concentrated in vacuo to give the title compound as an off-white solid (27 mg, 45%). MH+ 435

Workup

  1. temperaturethe mixture heated to 90° for 18 h under N2
  2. extractionextracted into ethyl acetate (4×10 ml)
  3. washThe combined organic phases were washed sequentially with water, brine, 2N sodium hydroxide and brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec3f1d9b0d7b449c9ddce2a6091522cd
Source dataset
uspto-grants-2007_05
Patent number
US07223772B1

Reaction notes

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