Potassium Carbonate → methyl 1-{2-[bis(tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl}-2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

HRID 1518223노트

반응식

HRID 1518223 반응식
[Br:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.N1C2C(=CC=C(C(OC)=O)C=2)C=C1.C([O-])([O-])=O.[K+].[K+].[C:40]([O:44][C:45]([N:47]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[C:48](=[CH2:53])[C:49]([O:51][CH3:52])=[O:50])=[O:46])([CH3:43])([CH3:42])[CH3:41]>CC#N>[C:40]([O:44][C:45]([N:47]([C:54]([O:56][C:57]([CH3:58])([CH3:60])[CH3:59])=[O:55])[CH:48]([C:49]([O:51][CH3:52])=[O:50])[CH2:53][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2)[C:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:2]1[Br:1])=[O:46])([CH3:43])([CH3:41])[CH3:42]

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 639844Methyl indole-6-carboxylateHCID 10870342Methyl 2-(bis((tert-butoxy)carbonyl)amino)prop-2-enoateHCID 11175076Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

생성물 1

HCID 68699898methyl 1-{2-[bis(tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl}-2-bromo-3-cyclohexyl-1H-indole-6-carboxylate수율 98%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (prepared from commercially available methyl indole-6-carboxylate as described in WO 2004/087714) in MeCN (0.2 M), 6.0 eq of K2CO3 and 1.0 eq of methyl 2-[bis(tert-butoxycarbonyl)amino]acrylate were added and the mixture was stirred overnight at RT. The mixture was then filtered and the filtrate concentrated in vacuo to afford the title compound (98%). MS (ES+) m/z 636 (M+H)+, MS (ES+) m/z 638 (M+H)+.

후처리

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate concentrated in vacuo

출처 및 근거

ORD 기록
ord-4bf23725326a401184298ca81b5d6102
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232390B2

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