Potassium Phosphate, Tribasic → HCID 58484562, compound

HRID 1804082Notes

Reaction equation

HRID 1804082 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:24])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:17]=[N:18][C:19]([F:23])=[CH:20][C:21]=3[CH3:22])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:33]1(B(O)O)[CH2:35][CH2:34]1>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH:33]1([C:2]2[CH:3]=[C:4]([CH3:24])[C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([C:16]4[CH:17]=[N:18][C:19]([F:23])=[CH:20][C:21]=4[CH3:22])=[O:15])[CH2:10][CH2:9]3)=[N:6][CH:7]=2)[CH2:35][CH2:34]1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 58484740HCID 58484740, compound

Product 1

HCID 58484562HCID 58484562, compoundYield 120.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(5-bromo-3-methylpyridin-2-yl)piperazin-1-yl](6-fluoro-4-methylpyridin-3-yl)methanone (2.2 g) described in Preparation Example 113 in tetrahydrofuran (15 mL) were added 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (229 mg), palladium acetate (125 mg), tripotassium phosphate (3.12 g) and cyclopropylboronic acid (721 mg), and the mixture was refluxed for 7 hr. After cooling, the mixture was extracted with ethyl acetate, washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography to give the title compound (2.39 g).

Workup

  1. temperaturethe mixture was refluxed for 7 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1d56672ae8d74a62ab55ca743201a53e
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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