Ammonium Chloride → Benzyl 3-(2-amino-1-(2-fluorophenyl)ethyl)-1H-indol-6-ylcarbamate

HRID 2361258노트

반응식

HRID 2361258 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[CH2:9][N+:10]([O-])=O.[Cl-].[NH4+]>O1CCCC1.CO.[Zn]>[NH2:10][CH2:9][CH:8]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 67994648Benzyl 3-(1-(2-fluorophenyl)-2-nitroethyl)-1H-indol-6-ylcarbamate

생성물 1

HCID 67995367Benzyl 3-(2-amino-1-(2-fluorophenyl)ethyl)-1H-indol-6-ylcarbamate수율 95.5%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of benzyl 3-(1-(2-fluorophenyl)-2-nitroethyl)-1H-indol-6-ylcarbamate (0.600 g, 1.384 mmol), zinc (1.358 g, 20.76 mmol), and ammonium chloride (1.111 g, 20.76 mmol) in tetrahydrofuran (30 mL) and methanol (30.0 mL) was stirred at room temperature for 2 hr. The insoluble material was removed by suction filtration through CELITE®. The filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (100 mL), washed with 10% NaHCO3 solution (25 mL) and brine (25 mL), and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (0.586 g, 1.322 mmol, 95% yield) as a pale white solid.

후처리

  1. customThe insoluble material was removed by suction filtration through CELITE®
  2. concentrationThe filtrate was concentrated under vacuum
  3. additionThe residue was diluted with ethyl acetate (100 mL)
  4. washwashed with 10% NaHCO3 solution (25 mL) and brine (25 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. customRemoval of solvent under vacuum

출처 및 근거

ORD 기록
ord-50e1ad01097241d0be5f687f2982f05a
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685969B2

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