Imidazole → 2-(4-(tert-butyldimethylsilyloxy)-2-methylbutan-2-yl)-6-fluoro-5-nitro-1H-indole

HRID 468515노트

반응식

HRID 468515 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([CH3:16])([CH3:15])[CH2:12][CH2:13][OH:14])[NH:8]2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1>C(Cl)Cl>[Si:24]([O:14][CH2:13][CH2:12][C:11]([C:7]1[NH:8][C:9]2[C:5]([CH:6]=1)=[CH:4][C:3]([N+:17]([O-:19])=[O:18])=[C:2]([F:1])[CH:10]=2)([CH3:16])[CH3:15])([C:21]([CH3:23])([CH3:22])[CH3:20])([CH3:26])[CH3:25]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 591293673-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutan-1-ol

생성물 1

HCID 591294122-(4-(tert-butyldimethylsilyloxy)-2-methylbutan-2-yl)-6-fluoro-5-nitro-1H-indole수율 52,558,400%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutan-1-ol (6.6 g, 25 mmol) in CH2Cl2 (80 mL) was added TBSCl (3.7 g, 25 nmol) and imidazole (4.2 g, 62 nmol) at 0° C. The reaction mixture was stirred at room temperature for 12 hours. The precipitate was filtered off and washed with the methanol. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 10:1) to give the desired product as a brown solid (5.0 g, 53%). 1H NMR (300 MHz, CDCl3) δ 9.80 (brs, 1H), 8.30 (d, J=7.2 Hz, 1H), 7.05 (d, J=11.7 Hz, 1H), 6.33 (t, J=1.2 Hz, 1H), 3.7 (t, J=6.0 Hz, 2H), 1.91 (t, J=6.0 Hz, 2H), 1.42 (s 6H), 0.94 (s, 9H), 0.12 (s, 6H). MS (ESI) m/z (M+H+): 381.1.

후처리

  1. filtrationThe precipitate was filtered off
  2. washwashed with the methanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 10:1)

출처 및 근거

ORD 기록
ord-5c20e7c076e440179896474f834d2db4
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

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