Benzyl Bromide → HCID 118021774, compound

HRID 518524Notes

Reaction equation

HRID 518524 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]([CH3:23])[CH:13]=2)[CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:23][N:14]1[CH:13]=[C:12]([C:4]2[CH:3]=[C:2]([O:1][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:22]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 118022255HCID 118022255, compound

Product 1

HCID 118021774HCID 118021774, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A capped mixture of 4-(3-hydroxy-5-methylsulfonylphenyl)-2-methylisoquinolin-1-one (25 mg, 0.076 mmol), benzyl bromide (20 mg, 0.12 mmol), and Cs2CO3 (50 mg, 0.15 mmol) in DMF (600 uL) was heated to 80° C. for 3 h. The mixture was filtered and the filter cake was washed with ACN (500 uL), the filtrate was purified by prep-HPLC to afford the title compound (12 mg, 38%) as a tan solid. LCMS (M+H)+=420.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with ACN (500 uL)
  3. customthe filtrate was purified by prep-HPLC

Sources & evidence

ORD record
ord-0912add8918f45449f7e2fc8a074bdc5
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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