Water → Methyl 2'-fluoro-2-(2-methyl-5-oxo-1-cyclopenten-1-yl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662450

반응식

HRID 1662450 반응식
Br[C:2]1[C:3](=[O:8])[CH2:4][CH2:5][C:6]=1[CH3:7].[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][C:19]=1B1OC(C)(C)C(C)(C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC.C1COCC1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][C:19]=1[C:2]1[C:3](=[O:8])[CH2:4][CH2:5][C:6]=1[CH3:7]

참가 물질

9

반응물 5

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 44370092-Bromo-3-methyl-2-cyclopenten-1-oneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57706776Methyl 2'-fluoro-5'-(methyloxy)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl-4-carboxylate

생성물 1

HCID 57705608Methyl 2'-fluoro-2-(2-methyl-5-oxo-1-cyclopenten-1-yl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate수율 78.1%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

A screw-cap vial was charged with 2-bromo-3-methyl-2-cyclopenten-1-one (available from Aldrich) (0.68 g, 3.9 mmol), 66.56A (1.00 g, 2.6 mmol), potassium phosphate (1.6 g, 7.8 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (available from Aldrich) (0.33 g, 0.80 mmol), palladium(II) acetate (available from Aldrich) (0.058 g, 0.26 mmol), degassed THF (17 mL), and water (0.23 mL, 13 mmol). The mixture was purged three times with N2, stirred for 48 hours at room temperature under N2, filtered through silica gel (EtOAc), and concentrated. Trituration of the crude residue with ether afforded 66.56B (0.72 g, 78% yield) as a pale yellow solid.

후처리

  1. customThe mixture was purged three times with N2
  2. filtrationfiltered through silica gel (EtOAc)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ef89c3da17274987b46d8285859673b9
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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