Cesium carbonate → 7-Chloro-6-fluoro-2-[(4-methoxyphenyl)methyl]isoquinolin-1(2H)-one

HRID 1621293Notes

Reaction equation

HRID 1621293 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][C:3]=1[F:13].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([CH2:26][C:25]3[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=3)[C:9]2=[O:12])=[CH:4][C:3]=1[F:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 598182487-Chloro-6-fluoroisoquinolin-1(2H)-one

Product 1

HCID 598182477-Chloro-6-fluoro-2-[(4-methoxyphenyl)methyl]isoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 g of 7-chloro-6-fluoro-2H-isoquinolin-1-one (60) were suspended in 100 mL of DMF. 19.75 g of cesium carbonate and 7.55 mL of p-methoxy benzyl chloride were added successively and the mixture was stirred for 2 h. The mixture was poured on ice/water and the formed precipitate was filtered off, washed with water and dried in vacuum to give 13.67 g of the title compound. Rt=1.96 min (Method B). Detected mass: 318.1 (M+H+).

Workup

  1. additionThe mixture was poured on ice/water
  2. filtrationthe formed precipitate was filtered off
  3. washwashed with water
  4. customdried in vacuum

Sources & evidence

ORD record
ord-300ac9df55054aeab821fcc9feb26e45
Source dataset
uspto-grants-2014_07
Patent number
US08772492B2

Reaction notes

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