Water → HCID 69002677, compound

HRID 1821330Notes

Reaction equation

HRID 1821330 reaction equation
[CH:1]([C:3]1[CH:28]=[CH:27][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2/[CH:16]=[CH:17]/[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][N:19]=2)=[O:8])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+].O>CO>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2/[CH:16]=[CH:17]/[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][N:19]=2)=[O:8])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86628199HCID 86628199, compound

Product 1

HCID 69002677HCID 69002677, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-4-formyl-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}benzamide (100 mg, 0.27 mmol) was dissolved in methanol (1.1 mL) and the solution was added with sodium borohydride (120 mg, 2.72 mmol), stirred at room temperature for 1 hour, added with water and extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was triturated in ethanol to obtain Compound 79 (10 mg, 10%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was sequentially washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was triturated in ethanol

Sources & evidence

ORD record
ord-011751d74bcd4cf684962a064b6857d0
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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