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

HRID 503310ノート

反応式

HRID 503310 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-dc0adbf72a954c4f877e520d26cf72a2
出典データセット
uspto-grants-2010_08
特許番号
US07776905B2

反応ノート

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