Potassium tert-butoxide → 5-bromo-6-cyclopropyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 531447Notes

Reaction equation

HRID 531447 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]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 900223295-Bromo-6-cyclopropyl-3-((trimethylsilyl)ethynyl)pyridin-2-amine

Product 1

HCID 900315195-bromo-6-cyclopropyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridineYield 121.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

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).

Workup

  1. customRM was quenched with water
  2. extractionextracted with ethyl acetate, organic portion
  3. dry with materialwas dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4a4d0242db0649d485a7a65a5ce1d475
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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