Potassium Phosphate, Tribasic → HCID 86630682, compound

HRID 1915576Notes

Reaction equation

HRID 1915576 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 example 31) and 0.12 g methylboronic acid in 17 ml toluene are added 0.83 g potassium phosphate tribasic, 0.029 g palladium acetate and 0.11 g S—PHOS. The reaction mixture is heated for 1 h under microwave irradiation to 120° C. This mixture is worked up by diluting with water and extraction with dichloromethane. The organic layers are dried over Na2SO4 and concentrated to yield the crude product, which is purified by chromatography on silica gel (ethyl acetate/dichloromethane).

Workup

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

Sources & evidence

ORD record
ord-2e567d8ae5344c699905b724ec644438
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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