Methylboronic Acid → HCID 71252709, compound

HRID 2411494Notes

Reaction equation

HRID 2411494 reaction equation
Cl[C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:30][CH2:29][CH2:28][S:27]4(=[O:32])=[O:31])=[CH:22][CH:21]=3)=[O:19])[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH:33]1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[F-].[K+].CB(O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCCC1>[O:31]=[S:27]1(=[O:32])[CH2:28][CH2:29][CH2:30][N:26]1[C:23]1[CH:24]=[CH:25][C:20]([C:18]([N:15]2[CH2:16][CH2:17][N:12]([C:3]3[C:2]([CH3:33])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=3)[CH2:13][CH2:14]2)=[O:19])=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 139377Methylboronic AcidHCID 522689Potassium FluorideHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 55433401HCID 55433401, compound

Product 1

HCID 71252709HCID 71252709, compoundYield 173.9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen stream, to a mixture of [4-(3-chloro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl]methanone (150 mg) described in Preparation Example 194, palladium(II) acetate (6.8 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (25.2 mg), potassium fluoride (141.2 mg) and methylboronic acid (73.6 mg) was added tetrahydrofuran (1.5 mL), and the mixture was stirred with heating under reflux for 8 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give the title compound (50 mg).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-aeaead5d96a047df833af22a4c1f0af6
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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