Benzyl Bromide → HCID 67420240, compound

HRID 625963Notes

Reaction equation

HRID 625963 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:8]([F:15])=[C:9]([OH:14])[C:10](=[O:13])[NH:11][CH:12]=2)[CH:2]=1.[OH-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CO>[CH2:24]([O:14][C:9]1[C:10](=[O:13])[NH:11][CH:12]=[C:7]([C:3]2[CH:2]=[C:1]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:6]=[CH:5][CH:4]=2)[C:8]=1[F:15])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 53379904HCID 53379904, compound

Product 1

HCID 67420240HCID 67420240, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5-biphenyl-3-yl-4-fluoro-3-hydroxypyridin-2(1H)-one (60 mg, 0.213 mmol) was added 1 N aqueous NaOH solution (0.235 mL, 0.235 mmol) and the resulting mixture was sonicated to make a clear solution. To this mixture was added a solution of benzyl bromide (37 mg, 0.213 mmol) in MeOH (0.3 mL) dropwise, stirred overnight at room temperature and then concentrated. Purification by preparative HPLC (10-70% CH3CN/H2O over 20 min, 0.05% added TFA) afforded 25 mg (32%) of 3-(benzyloxy)-5-(biphenyl-3-yl)-4-fluoropyridin-2(1H)-one as a white solid. LC/MS (M+H)+ 372.2.

Workup

  1. customthe resulting mixture was sonicated
  2. concentrationconcentrated
  3. customPurification
  4. additionby preparative HPLC (10-70% CH3CN/H2O over 20 min, 0.05% added TFA)

Sources & evidence

ORD record
ord-e2bda725ab7f48da9f6897892a3f452b
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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