Water → 6-Methyl-1H-pyrrolo[3,2-b]pyridine

HRID 2039860Notes

Reaction equation

HRID 2039860 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]#[C:10][Si](C)(C)C)[CH:5]=[N:6][CH:7]=1.CC([O-])(C)C.[K+].O>CN1C(=O)CCC1>[CH3:1][C:2]1[CH:3]=[C:4]2[NH:8][CH:9]=[CH:10][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 66922255HCID 66922255, compound

Product 1

HCID 213005726-Methyl-1H-pyrrolo[3,2-b]pyridineYield 75.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A solution of the compound of step 1 (5.12 g, 25.1 mmol) in NMP (125 ml) was added dropwise at room temperature to potassium tert-butylate (5.91 g, 52.6 mmol) in NMP (125 ml). The reaction mixture was stirred for 4 h at room temperature, then water was added and the aqueous phase was extracted with diethyl ether. The combined organic phases were dried over sodium sulfate, filtered and concentrated to give 2.5 g of the title compound.

Workup

  1. extractionthe aqueous phase was extracted with diethyl ether
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2248d5ffae05421a9c8ddfdd4fb4dabd
Source dataset
uspto-grants-2013_11
Patent number
US08580813B2

Reaction notes

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