Sodium borohydride → 1-(4-(6,7-Dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-4-(hydroxy(phenyl)methyl)pyrrolidin-2-one

HRID 1993388Notes

Reaction equation

HRID 1993388 reaction equation
[C:1]([CH:9]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[C:30]4[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=4)[N:24]=[CH:23][CH:22]=3)=[C:16]([F:35])[CH:15]=2)[C:11](=[O:36])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH3:32][O:31][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][C:27]=1[O:33][CH3:34])[N:24]=[CH:23][CH:22]=[C:21]2[O:20][C:17]1[CH:18]=[CH:19][C:14]([N:12]2[CH2:13][CH:9]([CH:1]([OH:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:10][C:11]2=[O:36])=[CH:15][C:16]=1[F:35]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118577274-Benzoyl-1-(4-(6,7-dimethoxyquinolin-4-yloxy)-3 fluorophenyl)pyrrolidin-2-one

Product 1

HCID 587517811-(4-(6,7-Dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-4-(hydroxy(phenyl)methyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-benzoyl-1-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenyl)pyrrolidin-2-one (Example 47, 0.2 g, 0.41 mmol) in 15 mL of MeOH was slowly added solid NaBH4 (50 mg, 1.32 mmol). The reaction was stirred at RT for 1 h. The reaction was quenched with 10 mL of satd. NH4Cl solution. The solution was diluted with 100 mL of EtOAc and was washed with 30 mL of satd. NH4Cl followed by 30 mL of brine, dried over Na2SO4 and concentrated in vacuo. The crude solid was purified by chromatography (EtOAc to 5% MeOH/EtOAc) to give a colorless film. MS (ESI pos. ion) m/z: 489.3 (M+H). Calc'd Exact Mass for C28H25FN2O5: 488.51.

Workup

  1. customThe reaction was quenched with 10 mL of satd
  2. additionThe solution was diluted with 100 mL of EtOAc
  3. washwas washed with 30 mL of satd
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude solid was purified by chromatography (EtOAc to 5% MeOH/EtOAc)
  7. customto give a colorless film

Sources & evidence

ORD record
ord-e6012d21dfc246ac98196d84ce523887
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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