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

HRID 1023820노트

반응식

HRID 1023820 반응식
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.[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.O>[Cl:19][C:20]1[CH:25]=[C:24]([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:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 86658779tert-butyl ((1R,2S)-2-(4-bromophenyl)cyclopropyl)carbamate2회

생성물 1

HCID 86680872Tert-butyl(trans)-2-(3'-chlorobiphenyl-4-yl)cyclopropylcarbamate수율 91%

시약·촉매·용매 1

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

실험 절차

A solution of tert-butyl (trans)-2-(4-bromophenyl)cyclopropylcarbamate (Intermediate H, 3 g, 9.6 mmol), 3-chlorophenylboronic acid (1.8 g, 11.5 mmol) and K2CO3 (3.9 g, 28.8 mmol) in acetonitrile:water (4:1) was degassed for 20 min. Tetrakis triphenylphosphine palladium (300 mg) was added and heated at reflux for 18 h. After completion, the reaction mixture was poured into ice water (100 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL) and dried over anhydrous Na2SO4 filtered and evaporated. The crude residue was purified by column chromatography (SiO2) using EtOAc: Pet ether to give (3 g, 91%) tert-butyl (trans)-2-(3′-chlorobiphenyl-4-yl)cyclopropylcarbamate as a white solid.

후처리

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude residue was purified by column chromatography (SiO2)

출처 및 근거

ORD 기록
ord-fe25649eba4b429a8a8fca3560739bf3
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722743B2

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