t-Butyl bromide → 3-(tert-Butyl)-6-nitro-1h-indole

HRID 73930

반응식

HRID 73930 반응식
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(C(C)C)C(C)C.[C:22](Br)([CH3:25])([CH3:24])[CH3:23]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].C1(C)C=CC=CC=1.[O-]S(C(F)(F)F)(=O)=O.[Zn+2].[O-]S(C(F)(F)F)(=O)=O>[C:22]([C:8]1[C:7]2[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[NH:10][CH:9]=1)([CH3:25])([CH3:24])[CH3:23]

참가 물질

7

반응물 3

HCID 10485t-Butyl bromideHCID 785026-Nitro-1H-indoleHCID 81531Diisopropylethylamine

생성물 1

HCID 574701983-(tert-Butyl)-6-nitro-1h-indole수율 22.2%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 104671Zinc trifluoromethanesulfonate촉매HCID 1140Toluene용매

반응 조건

온도
120 °C

실험 절차

To a mixture of 6-nitroindole (1 g, 6.2 mmol), zinc triflate (2.06 g, 5.7 mmol) and TBAI (1.7 g, 5.16 mmol) in anhydrous toluene (11 mL) was added DIEA (1.47 g, 11.4 mmol) at room temperature under nitrogen. The reaction mixture was stirred for 10 min at 120° C., followed by addition of t-butyl bromide (0.707 g, 5.16 mmol). The resulting mixture was stirred for 45 min at 120° C. The solid was filtered off and the filtrate was concentrated to dryness and purified by column chromatography on silica gel (Pet.Ether./EtOAc 20:1) to give 3-tert-butyl-6-nitro-1H-indole as a yellow solid (0.25 g, 19%). 1H NMR (CDCl3) δ 8.32 (d, J=2.1 Hz, 1H), 8.00 (dd, J=2.1, 14.4 Hz, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.25 (s, 1H), 1.46 (s, 9H).

후처리

  1. stirringThe resulting mixture was stirred for 45 min at 120° C
  2. filtrationThe solid was filtered off
  3. concentrationthe filtrate was concentrated to dryness
  4. custompurified by column chromatography on silica gel (Pet.Ether./EtOAc 20:1)

출처 및 근거

ORD 기록
ord-f2ad71930ecb4773ba351e9d93c9dc4e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

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