Water → HCID 59407818, compound

HRID 1093477Notes

Reaction equation

HRID 1093477 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31](Br)=[CH:30][CH:29]=3)=[C:20]([C:35]([F:38])([F:37])[F:36])[CH:19]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:48]1(B(O)O)[CH2:50][CH2:49]1.O>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[C:1]([O:5][C:6](=[O:39])[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([CH:48]4[CH2:50][CH2:49]4)=[CH:30][CH:29]=3)=[C:20]([C:35]([F:38])([F:37])[F:36])[CH:19]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 962Water2×HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 59407728HCID 59407728, compound

Product 1

HCID 59407818HCID 59407818, compoundYield 93.9%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

Compound 41-4 (500 mg) was dissolved in tetrahydrofuran (1.6 ml), tripotassium phosphate (430 mg), palladium acetate (9.0 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (17 mg), cyclopropylboronic acid (85 mg) and water (40 μl) were added, and the mixture was stirred at 100° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give the object product (440 mg) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-518a027e4cfe47289a7d30d7cfdff5f3
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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