3-formyl-N-methyl-1H-indole-2-carboxamide → N-methyl-3-vinyl-1H-indole-2-carboxamide

HRID 1362432ノート

反応式

HRID 1362432 の反応式
[CH2:1]([Li])CCC.[CH:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[C:17]([NH:19][CH3:20])=[O:18])=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:20][NH:19][C:17]([C:9]1[NH:10][C:11]2[C:16]([C:8]=1[CH:6]=[CH2:1])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:18]

参加物

5

反応物 2

HCID 592775763-formyl-N-methyl-1H-indole-2-carboxamideHCID 178418339Butyllithium

生成物 1

HCID 59277607N-methyl-3-vinyl-1H-indole-2-carboxamide

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

n-Butyllithium (2.5M in hexanes) (48.6 mL, 121.7 mmol) was added dropwise to an ice-cooled solution of methyl triphenylphosphoniumbromide (43.5 g, 121.7 mmol) in THF (500 mL). The mixture was stirred at 0° C. for 1 h then at rt for 2 h. 3-Formyl-N-methyl-1H-indole-2-carboxamide (1.96 g, 9.7 mmol) in THF (100 mL) was added and the mixture stirred at rt for 2 h. The solvent was evaporated and the residue dissolved in ethyl acetate and washed twice with water. The organic phase was dried over magnesium bromide and evaporated in vacuo. The crude mixture was chromatographed over silica gel eluting with 40% ethyl acetate in hexanes to afford the title compound (730 mg (38%). 1H NMR (300 MHz, DMSO-d6) δ 11.48 (s, 1H), 8.04 (s, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.42 (d, J=7.9 Hz, 1H), 7.33 (d, J=18 Hz, 1H), 7.22 (t, J=7.6 Hz, 1H), 7.09 (t, J=7.2 Hz, 1H), 5.77 (d, J=18.4 Hz, 1H), 5.27 (d, J=11.6 Hz, 1H), 2.81 (s, 3H).

後処理

  1. waitat rt for 2 h
  2. stirringthe mixture stirred at rt for 2 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed twice with water
  6. dry with materialThe organic phase was dried over magnesium bromide
  7. customevaporated in vacuo
  8. customThe crude mixture was chromatographed over silica gel eluting with 40% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-bf6c3458b0d241eea6965562d02d7568
出典データセット
uspto-grants-2011_02
特許番号
US07879872B2

反応ノート

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