Water → HCID 59407886, compound

HRID 1093481Notes

Reaction equation

HRID 1093481 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][CH:31]=[C:30](Br)[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][CH:31]=[C:30]([CH:48]4[CH2:50][CH2:49]4)[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 59407791HCID 59407791, compound

Product 1

HCID 59407886HCID 59407886, compoundYield 88%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

Compound 40-4 (400 mg) was dissolved in tetrahydrofuran (1.3 ml), tripotassium phosphate (350 mg), palladium acetate (7.2 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (13 mg) and cyclopropylboronic acid (80 mg) were added, and the mixture was stirred at 80° C. for 2 hr. Water (30 μl) was added, and the mixture was further stirred for 5.5 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 (330 mg) as a white solid.

Workup

  1. stirringthe mixture was further stirred for 5.5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-2d960deaa5b74646920c397c26619602
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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