Potassium tert-butoxide → 5-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 402596

Reaction equation

HRID 402596 reaction equation
CC(C)([O-])C.[K+].[NH2:7][C:8]1[C:13]([C:14]#[C:15][Si](C)(C)C)=[CH:12][C:11]([Cl:20])=[CH:10][N:9]=1>CN1CCCC1=O.[Cl-].[Na+].O>[Cl:20][C:11]1[CH:12]=[C:13]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:15]=[CH:14]2

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 247294655-Chloro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

Product 1

HCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere, to a solution of potassium tert-butoxide (4.0 g, 0.036 mol) in 1-methyl-2-pyrrolidone (8.0 mL) which stirred with heating at 80° C., a solution of 2-amino-5-chloro-3-[(trimethylsilyl)ethynyl]pyridine (4.0 g, 0.018 mol) in 1-methyl-2-pyrrolidone (22 mL) was added dropwise and the mixture was stirred for 1 h. Cooled to ambient temperature, the reaction mixture was diluted with brine and stirred, then extracted with diethyl ether for 3 times. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford 5-chloro-7-azaindole as solid (2.3 g, y. 85%).

Workup

  1. temperatureCooled to ambient temperature
  2. stirringstirred
  3. extractionextracted with diethyl ether for 3 times
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1c9338128f2b4d4896b90c169b620e39
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Linked notes

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