Reaction #2146768

ord-f911de9cc60649dd8d2b5c58806e4ec9

Reaction equation

COc1ccc(CCl)cc1
p-methoxybenzylchloride
O=c1[nH]ccc2cc(F)ccc12
6-fluoro-isoquinolinone
O=C([O-])[O-].[Cs+].[Cs+]
Cs2CO3
COc1ccc(Cn2ccc3cc(F)ccc3c2=O)cc1
title compound
Yield 93.7%
COc1ccc(Cn2ccc3cc(F)ccc3c2=O)cc1
6-Fluoro-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one
Yield 93.7%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONpoured on ice
  2. 2
    FiltrationThe precipitate was filtered
  3. 3
    Washwashed with water
  4. 4
    Otherdried

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]+

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08278294B2uspto-grants-2012_10