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

HRID 347560노트

반응식

HRID 347560 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

HCID 210816754-Chloro-2-methyl-7-azaindole수율 60.6%

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-f61b5f9916b1442abd59ad92987b11ad
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173031B2

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