三氟乙酸 → N-[3-(1-ethyl-5-fluoro-indan-1-yl)-1H-indol-7-yl]-methanesulfonamide

HRID 13699

反应方程式

HRID 13699 反应方程式
[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]

参与物

5

反应物 3

HCID 6422三氟乙酸HCID 20231824n-(1h-Indol-7-yl)methanesulfonamideHCID 593404281-Ethyl-5-fluoroindan-1-ol

产物 1

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

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

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.

后处理

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

来源与证据

ORD记录
ord-fbe7d318a9d74414884f73b6d827b33f
来源数据集
uspto-grants-2010_06
专利号
US07728150B2

关联笔记

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