Sodium borohydride → Veonetinib

HRID 1510105Notes

Reaction equation

HRID 1510105 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][N:27]4[CH2:33][C:32](=[O:34])[C:29]5([CH2:31][CH2:30]5)[CH2:28]4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:35])[NH:6]2.[BH4-].[Na+]>CO>[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][N:27]4[CH2:33][CH:32]([OH:34])[C:29]5([CH2:31][CH2:30]5)[CH2:28]4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:35])[NH:6]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 461764815-(2-(4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxyquinolin-7-yloxy)ethyl)-5-azaspiro[2.4]-heptan-7-one

Product 1

HCID 46176482VeonetinibYield 79.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above product from Example 2 (75 mg) was dissolved into MeOH (8 ml) and stirred at RT. NaBH4 (75 mg) was added to the reaction and stirred at RT for 30 min. The reaction was evaporated and purified by column chromatography to give title compound (60 mg). Mass: (M+1), 478

Workup

  1. stirringstirred at RT for 30 min
  2. customThe reaction was evaporated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-b7948eb6f2c34b8abef886925e5ac23b
Source dataset
uspto-grants-2012_07
Patent number
US08211911B2

Reaction notes

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