Potassium tert-butoxide → 5-bromo-6-cyclopropyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:5]([NH2:11])=[N:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH:12]=[C:13]([Si:14]([CH3:16])([CH3:15])[CH3:17])[NH:11][C:5]2=[N:6][C:7]=1[CH:8]1[CH2:9][CH2:10]1Participants
4
Procedure
A stirred solution of 5-bromo-6-cyclopropyl-3-((trimethylsilyl)ethynyl)pyridin-2-amine (1 g, 3.2 mmol), tert-butanol (10 mL) was added potassium tert-butoxide (1.45 g, 12.9 mmol) and stirred at ambient temperature for 15 min. RM was quenched with water and extracted with ethyl acetate, organic portion was dried over sodium sulfate and concentrated to give 1.2 g of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 7.86-7.85 (m, 1H), 6.45-6.42 (m, 1H), 4.98-4.96 (m, 1H), 4.88-4.7 (m, 1H), 4.55 (s, 2H), 2.35-2.31 (m, 1H), 2.0 (s, 9H), 1.04-0.86 (m, 4H). LCMS: m/z=311.1 (M+1).