Sodium borohydride → 3-Chloro-2-methyl-7-(2-phenyl-2-hydroxyethyl)pyrrolo-[2,3-b]pyridine

HRID 1756052Notes

Reaction equation

HRID 1756052 reaction equation
Cl.[Cl:2][C:3]1[C:11]2[C:6]([N:7]([CH2:12][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:14])[CH:8]=[CH:9][CH:10]=2)=[N:5][C:4]=1[CH3:21].[BH4-].[Na+]>CO>[Cl:2][C:3]1[C:11]2[C:6]([N:7]([CH2:12][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[OH:14])[CH:8]=[CH:9][CH:10]=2)=[N:5][C:4]=1[CH3:21]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 193926053Chloro-2-methyl-7-phenacylpyrrolo-[2,3-b]pyridinehydrochloride

Product 1

HCID 199167653-Chloro-2-methyl-7-(2-phenyl-2-hydroxyethyl)pyrrolo-[2,3-b]pyridineYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 120 mg (0,37 mmol) of 3-chloro-2-metyl-7-phenacylpyrrolo[2,3-b]pyridine hydrochlorid in 2 ml methanol was added 30 mg (0,79mmol) of sodium borohydride. The mixture was stirred for 20 h at room temperature. The solvent was evaporated and the residue was partitioned between 2 ml of 0,2M hydrochloric acid and 2 ml of ethyl acetate. The aqueos layer was basified by addition of 2M sodium hydroxide and extracted twice with 2 ml of methylene chloride. The combined organic phase was dried over sodium sulfate and the solvent was evaporated. The residue was treated with acetonitrile and the precipitate was filtered off to give 20 mg (19%) 3-chloro-2-methyl-7-(2-phenyl-2-hydroxyethyl)pyrrolo-[2,3-b]pyridine.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between 2 ml of 0,2M hydrochloric acid and 2 ml of ethyl acetate
  3. additionThe aqueos layer was basified by addition of 2M sodium hydroxide
  4. extractionextracted twice with 2 ml of methylene chloride
  5. dry with materialThe combined organic phase was dried over sodium sulfate
  6. customthe solvent was evaporated
  7. additionThe residue was treated with acetonitrile
  8. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-4672fc00d3d34e1782e33852953f3955
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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