Cesium carbonate → 6-Fluoro-2-[(4-methoxyphenyl)methyl]isoquinolin-1-one

HRID 1930204Notes

Reaction equation

HRID 1930204 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[F:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[NH:17][CH:16]=[CH:15]2.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[N:17]([CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH:16]=[CH:15]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 450908026-Fluoroisoquinolin-1(2H)-one

Product 1

HCID 598182606-Fluoro-2-[(4-methoxyphenyl)methyl]isoquinolin-1-oneYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

169 μL of p-methoxybenzylchloride (1.24 mmol, 1.1 eq) were added to a suspension of 200 mg of 6-fluoro-isoquinolinone (13) (1.13 mmol) and 368 mg of Cs2CO3 (1.36 mmol, 1.2 eq) in 3 mL of DMF. The mixture was stirred for 2 h and then poured on ice. The precipitate was filtered, washed with water and dried to yield 300 mg of the title compound. LCMS Method B, retention time 1.76 min, detected mass 284.14 [M+H]+

Workup

  1. additionpoured on ice
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-69a7ed0ca77341ce88ef0eeaab37f2c0
Source dataset
uspto-grants-2012_05
Patent number
US08188117B2

Reaction notes

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