Methyl iodide → HCID 67417904, compound

HRID 625964Notes

Reaction equation

HRID 625964 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:28])[NH:11][CH:12]=[C:13]([C:16]2[CH:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:19]=[CH:20][CH:21]=2)[C:14]=1[F:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10](=[O:28])[N:11]([CH3:29])[CH:12]=[C:13]([C:16]2[CH:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:19]=[CH:20][CH:21]=2)[C:14]=1[F:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 67420240HCID 67420240, compound

Product 1

HCID 67417904HCID 67417904, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-(benzyloxy)-5-(biphenyl-3-yl)-4-fluoropyridin-2(1H)-one (24 mg, 0.065 mmol) in DMF (0.8 mL) was added Cs2CO3 (27 mg, 0.084 mmol) followed by a solution of MeI (10 mg, 0.071 mmol) in DMF (0.05 mL). After stirring at room temperature for 1 h the reaction mixture was filtered. Purification by preparative HPLC (10-80% CH3CN/H2O over 20 min, 0.05% added TFA) afforded 22 mg (88%) of 3-(benzyloxy)-5-(biphenyl-3-yl)-4-fluoro-1-methylpyridin-2(1H)-one as a colorless glass. LC/MS (M−141)+ 296.2.

Workup

  1. filtrationwas filtered
  2. customPurification
  3. additionby preparative HPLC (10-80% CH3CN/H2O over 20 min, 0.05% added TFA)

Sources & evidence

ORD record
ord-9d1f5d83c3724ad880e7a181774e388d
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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