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

HRID 1662450

反応式

HRID 1662450 の反応式
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]

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-ef89c3da17274987b46d8285859673b9
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

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