Water → 2-Tert-butyl-6-fluoro-5-nitro-1H-indole

HRID 503310노트

반응식

HRID 503310 반응식
[CH3:1][C:2]([CH3:22])([CH3:21])[C:3]#[C:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([F:14])=[CH:7][C:6]=1[NH:15]C(=O)CCC.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>CN(C=O)C>[C:2]([C:3]1[NH:15][C:6]2[C:5]([CH:4]=1)=[CH:10][C:9]([N+:11]([O-:13])=[O:12])=[C:8]([F:14])[CH:7]=2)([CH3:22])([CH3:21])[CH3:1]

참가 물질

5

반응물 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59129414N-(2-(3,3-dimethylbut-1-ynyl)-5-fluoro-4-nitrophenyl)butyramide

생성물 1

HCID 534211862-Tert-butyl-6-fluoro-5-nitro-1H-indole수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of N-(2-(3,3-dimethylbut-1-ynyl)-5-fluoro-4-nitrophenyl)butyramide (3.0 g, 9.8 mmol) and TBAF (4.5 g, 17.2 mmol) in DMF (25 mL) was heated at 100° C. overnight. The mixture was poured into water and then extracted with EtOAc (80 mL×3). The combined extracts were washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to dryness. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1) to give compound 2-tert-butyl-6-fluoro-5-nitro-1H-indole (1.5 g, 65%). 1H-NMR (400 MHz, CDCl3) δ 8.30 (d, J=7.2 Hz, 1H), 7.12 (d, J=11.6 Hz, 1H), 6.35 (d, J=1.2 Hz, 1H), 1.40 (s, 9H).

후처리

  1. extractionextracted with EtOAc (80 mL×3)
  2. washThe combined extracts were washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure to dryness
  5. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1)

출처 및 근거

ORD 기록
ord-dc0adbf72a954c4f877e520d26cf72a2
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776905B2

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