Potassium Carbonate → Tert-butyl(trans)-2-(3'-(trifluoromethyl)biphenyl-4-yl)cyclopropylcarbamate

HRID 1470550

反応式

HRID 1470550 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:25][C:26]([F:37])([F:36])[C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1>C(#N)C.O>[F:25][C:26]([F:37])([F:36])[C:27]1[CH:32]=[C:31]([C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]3[CH2:10][C@H:9]3[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=2)[CH:30]=[CH:29][CH:28]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 86658779tert-butyl ((1R,2S)-2-(4-bromophenyl)cyclopropyl)carbamate

生成物 1

HCID 86673371Tert-butyl(trans)-2-(3'-(trifluoromethyl)biphenyl-4-yl)cyclopropylcarbamate収率 66.2%

試薬・触媒・溶媒 1

HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

To a solution of tert-butyl (trans)-2-(4-bromophenyl)cyclopropylcarbamate (Intermediate E[a2]) (1 g, 3.2 mmol), potassium carbonate (1.31 g, 9.6 mmol), 3-(trifluoromethyl) phenylboronic acid (0.73 g, 3.8 mmol) in acetonitrile:water (4:1) were degassed for 30 mins, added tetrakis triphenylphosphine palladium (36 mg, 0.032 mmol), degassed again for 10 mins, heated the reaction mixture at reflux temperature for 5 h. After completion, the reaction mixture was poured in ice water (50 mL), extracted with, ethyl acetate (2×50 mL). Combined extracts were washed with water (70 mL), brine (70 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by column chromatography (SiO2), by using EtOAc:Petroleum ether (2:8) to get tert-butyl (trans)-2-(3′-(trifluoromethyl)biphenyl-4-yl)cyclopropylcarbamate (0.8 g, 66%) as a white solid.

後処理

  1. customdegassed again for 10 mins
  2. temperatureheated the reaction mixture
  3. temperatureat reflux temperature for 5 h
  4. additionAfter completion, the reaction mixture was poured in ice water (50 mL)
  5. extractionextracted with, ethyl acetate (2×50 mL)
  6. washCombined extracts were washed with water (70 mL), brine (70 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude residue was purified by column chromatography (SiO2)

出典と根拠

ORDレコード
ord-9ff134d1486d41a2a690bc1caa39c725
出典データセット
uspto-grants-2015_04
特許番号
US09006449B2

関連ノート

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