Tetrabutylammonium Fluoride → 4-Chloro-2-methyl-7-azaindole

HRID 347560ノート

反応式

HRID 347560 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](COCC[Si](C)(C)C)[C:9]([CH3:11])=[CH:10][C:3]=12.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([CH3:11])=[CH:10][C:3]=12

参加物

3

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 210816744-Chloro-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 210816754-Chloro-2-methyl-7-azaindole収率 60.6%

実験手順

A mixture of 4-chloro-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo-[2,3-b]pyridine (296.5 mg, 1 mmol) and TBAF (5 mL, 1 M in THF, Aldrich) was refluxed overnight. The THF was removed under reduced pressure and the residue was diluted with water (5 mL). The precipitate that formed was collected, washed with water and dried (MgSO4) to afford the title compound (101 mg, 60%). 1H NMR (CD3OD) δ 7.99 (d, 1H, J=5.5 Hz), 7.06 (d, 1H, J=5.5 Hz), 6.23 (s, 1H), 2.46 (s, 3H); MS(ESI+) m/z 167 and 169 (M+H, 1 Cl)+.

後処理

  1. temperaturewas refluxed overnight
  2. customThe THF was removed under reduced pressure
  3. additionthe residue was diluted with water (5 mL)
  4. customThe precipitate that formed
  5. customwas collected
  6. washwashed with water
  7. dry with materialdried (MgSO4)

出典と根拠

ORDレコード
ord-f61b5f9916b1442abd59ad92987b11ad
出典データセット
uspto-grants-2007_02
特許番号
US07173031B2

反応ノート

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