Dimethylformamide → Methyl 5'-chloro-2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-1,1'-biphenyl-4-carboxylate

HRID 1662517ノート

反応式

HRID 1662517 の反応式
C1([C@H](C2C=CC=C(OC[C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[C:27](OC)[CH:26]=[CH:25][C:24]=4F)=[C:19]([C@H:32](O)C(C)(C)C=C)[CH:18]=3)C=2)CC(O)=O)CC1.[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([F:49])=[C:44](B(O)O)[CH:45]=1.[C:50](=[O:53])([O-])[O-:51].[K+].[K+].[CH3:56]N(C=O)C>[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([F:49])=[C:44]([C:28]2[CH:27]=[CH:26][C:25]([C:50]([O:51][CH3:56])=[O:53])=[CH:24][C:23]=2[C:20]2[C:19]([CH3:18])([CH3:32])[CH2:17][CH2:22][CH:21]=2)[CH:45]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3718925(5-Chloro-2-fluoro-phenyl)boronic acidHCID 57705953HCID 57705953、化合物

生成物 1

HCID 57706006Methyl 5'-chloro-2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-1,1'-biphenyl-4-carboxylate収率 86%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
90 °C

実験手順

To a stirred solution of methyl 3-(5,5-dimethylcyclopent-1-enyl)-4-(trifluoromethylsulfonyloxy)benzoate 66.61 (0.100 g, 0.3 mmol) in DMF (4 mL) at 23° C. was added 5-chloro-2-fluorophenylboronic acid (0.07 g, 0.4 mmol) (commercially available from Aldrich), potassium carbonate (0.1 g, 0.8 mmol), followed by tetrakis(triphenylphosphine)palladium (0.03 g, 0.03 mmol). The mixture was heated to 90° C. and stirring was continued for 23 hours. The reaction was then cooled to room temperature. The reaction was diluted with brine and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was purified on silica gel (0-10% EtOAc in hexanes) to yield 78.9A as a colorless oil (0.082 g, 86% yield).

後処理

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure
  6. customthe product was purified on silica gel (0-10% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-a7ebf87dedfc42cfbb1ef9bfaa7ba955
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

反応ノート

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