Ammonia → 4-Chloro-1H-pyrrolo[2,3-b]pyridin-6-amine

HRID 888133Notes

Reaction equation

HRID 888133 reaction equation
ClC1C=C(C=CC=1)C(O)=O.[Cl:11][C:12]1[CH:20]=[CH:19][NH:18][C:17]2[C:13]=1[CH:14]=[CH:15][N+:16]=2[O-].COS(OC)(=O)=O.[NH3:29]>C(C#N)(C)=O.CCO>[Cl:11][C:12]1[CH:20]=[C:19]([NH2:29])[N:18]=[C:17]2[NH:16][CH:15]=[CH:14][C:13]=12

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6497Dimethyl SulfateHCID 178524354HCID 178524354, compound

Product 1

HCID 534083654-Chloro-1H-pyrrolo[2,3-b]pyridin-6-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 694302-OxopropiononitrileSolvent

Conditions

Temperature
57.5 °C

Procedure

To a suspn. of 4-chloro-7-azaindole-N-oxide m-chlorobenzoic acid salt [J. Org. Chem. 1980, 45, 4045] (1.60 g, 4.92 mmol) in AcCN (10 ml) was added dimethylsulfate (0.50 ml, 1.05 eq.) at RT. The suspn. was stirred under N2 at 55-60° C. overnight. After cooling to RT, a solution of NH3 in dry EtOH (2M, Aldrich, 20 ml) under cooling in an ice bath. The greenish mixture was stirred in a sealed vial at RT for 4 h, then at 45° C. for 60 h. After evaporation of the solvent and aq. workup as in the previous examples, the crude was purified by silica gel chromatography to give a yellowish-tan cryst. solid. HR-MS calculated for [MH]+: 168.03230, found: 168.03218.

Workup

  1. temperatureAfter cooling to RT
  2. stirringThe greenish mixture was stirred in a sealed vial at RT for 4 h
  3. waitat 45° C. for 60 h
  4. customAfter evaporation of the solvent and aq. workup as in the previous examples
  5. customthe crude was purified by silica gel chromatography
  6. customto give a yellowish-tan cryst

Sources & evidence

ORD record
ord-8cef75fa058048d6a36359cb34672a8a
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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