Tetrabutylammonium Fluoride → HCID 59129336、化合物

HRID 468360ノート

反応式

HRID 468360 の反応式
[CH3:1][C:2]1([C:5]#[C:6][C:7]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=2[NH:16]C(=O)CCC)[CH2:4][CH2:3]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][C:2]1([C:5]2[NH:16][C:8]3[C:7]([CH:6]=2)=[CH:12][C:11]([N+:13]([O-:15])=[O:14])=[CH:10][CH:9]=3)[CH2:4][CH2:3]1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 59129340N-(2-(1-methyl-cyclopropylethynyl)-4-nitro-phenyl]-butyramide

生成物 1

HCID 59129336HCID 59129336、化合物収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of N-[2-(1-methyl-cyclopropylethynyl)-4-nitro-phenyl]-butyramide (1.3 g, 4.6 mmol) and TBAF (2.4 g, 9.2 mmol) in THF (20 mL) was heated at reflux for 24 h. The mixture was cooled to room temperature and poured into ice water. The mixture was extracted with CH2Cl2 (30 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1) to afford 2-(1-methylcyclopropyl)-5-nitro-1H-indole (0.70 g, 71%). 1H NMR (400 MHz, CDCl3) δ 8.56 (brs, 1H), 8.44 (d, J=2.0 Hz, 1H), 8.01 (dd, J=2.4, 8.8 Hz, 1H), 7.30 (d, J=8.8 Hz, 1H), 6.34 (d, J=1.6 Hz, 1H), 1.52 (s, 3H), 1.03-0.97 (m, 2H), 0.89-0.83 (m, 2H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. extractionThe mixture was extracted with CH2Cl2 (30 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1)

出典と根拠

ORDレコード
ord-2e8eba46c2e74776acb4e8fc2ae6fd80
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

反応ノート

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