Potassium Phosphate, Tribasic → HCID 86630682, compound

HRID 1851205Notes

Reaction equation

HRID 1851205 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([C:17]3[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=3)=[N:7][C:6]=12.[CH3:25]B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C1(C)C=CC=CC=1.O.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:25][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([C:17]3[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=3)=[N:7][C:6]=12

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86630675HCID 86630675, compound

Product 1

HCID 86630682HCID 86630682, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 0.50 g 4-(3-bromo-6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde (prepared as described under intermediate example 23) and 0.12 g methylboronic acid in 17 mL toluene were added 0.83 g potassium phosphate tribasic, 0.029 g palladium acetate and 0.11 g S-PHOS. The reaction mixture was heated for 1 h under microwave irradiation to 120° C. This mixture was worked up by diluting with water and extraction with dichloromethane. The organic layers were dried over Na2SO4 and concentrated to yield the crude product, which was purified by chromatography on silica gel (ethyl acetate/dichloromethane).

Workup

  1. dry with materialThe organic layers were dried over Na2SO4
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c2ffa744c0274de9be2ec234606fff1c
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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