Sodium borohydride → HCID 54044688, compound

HRID 1756086Notes

Reaction equation

HRID 1756086 reaction equation
[Cl:1][C:2]1[N:19]=[C:5]2[N:6]([CH2:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])[CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH2:20][C:21]#[N:22].[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:19]=[C:5]2[N:6]([CH2:10][CH:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[OH:12])[CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH2:20][C:21]#[N:22]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19916784HCID 19916784, compound

Product 1

HCID 54044688HCID 54044688, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-chloro-3-cyanomethyl-7-phenacylpyrrolo(2,3-b]pyridine (15 mg 0.05 mmol) in 3 ml MeOH was treated with 10 mg NaBH4 and allowed to react for 30 min at room temperature. The solvent was evaporated and the residue partitioned between CH2Cl2 and water. The organic layer was separated, dried over Na2SO4 and evaporated. Chromatography on silica gel eluting with ether gave the desired product (7 mg 46%).

Workup

  1. customto react for 30 min at room temperature
  2. customThe solvent was evaporated
  3. customthe residue partitioned between CH2Cl2 and water
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-ad2d464e2f4541f7bdfa66d4f0330d59
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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