Trifluoroacetic acid → N-[3-(1-ethyl-5-fluoro-indan-1-yl)-1H-indol-7-yl]-methanesulfonamide

HRID 13699

반응식

HRID 13699 반응식
[CH2:1]([C:3]1(O)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:16]=[CH:15]1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([C:3]1([C:16]2[C:17]3[C:22](=[C:21]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])[CH:20]=[CH:19][CH:18]=3)[NH:14][CH:15]=2)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 20231824n-(1h-Indol-7-yl)methanesulfonamideHCID 593404281-Ethyl-5-fluoroindan-1-ol

생성물 1

HCID 11268772N-[3-(1-ethyl-5-fluoro-indan-1-yl)-1H-indol-7-yl]-methanesulfonamide수율 84.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Combine 1-ethyl-5-fluoro-indan-1-ol (502 mg, 2.79 mmol, 1.30 equivalents), N-(1H-Indol-7-yl)-methanesulfonamide (450 mg, 2.14 mmol, 1.00 equivalents), and trifluoroacetic acid (0.25 ml, 3.21 mmol, 1.50 equivalents) in dichloromethane (5 ml) and stir at room temperature under nitrogen overnight. Load the solution on silica and purify eluting with 0 to 100% ethyl acetate/hexanes over 25 minutes to obtain the title compound (672 mg, 84%). LC-MS m/z 373.0 (M++1). The racemic mixture is separated on a Chiralcel OJ 8×33 cm column eluting with methanol with 0.2% dimethylethylamine (flow: 375 ml/min, UV detection at 230 nm) to provide the individual enantiomers, Examples 1A and 1B, in 96.3% ee and 97.4% ee, respectively.

후처리

  1. customLoad the solution on silica and purify
  2. washeluting with 0 to 100% ethyl acetate/hexanes over 25 minutes

출처 및 근거

ORD 기록
ord-fbe7d318a9d74414884f73b6d827b33f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728150B2

연결된 노트

불러오는 중…