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

HRID 347560Notes

Reaction equation

HRID 347560 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-f61b5f9916b1442abd59ad92987b11ad
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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