Anisole → 6-(4-(1H-pyrazol-1-yl)benzyl)-5-methylisoindolin-1-one

HRID 629345Notes

Reaction equation

[N:1]1([C:6]2[CH:34]=[CH:33][C:9]([CH2:10][C:11]3[CH:19]=[C:18]4[C:14]([CH2:15][N:16](CC5C=CC(OC)=CC=5OC)[C:17]4=[O:20])=[CH:13][C:12]=3[CH3:32])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[N:1]1([C:6]2[CH:34]=[CH:33][C:9]([CH2:10][C:11]3[CH:19]=[C:18]4[C:14]([CH2:15][NH:16][C:17]4=[O:20])=[CH:13][C:12]=3[CH3:32])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-(4-(1H-pyrazol-1-yl)benzyl)-2-(2,4-dimethoxybenzyl)-5-methylisoindolin-1-one (0.24 g) in trifluoroacetic acid (4.34 mL) was added anisole (0.23 mL), and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.15 g).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-2c61fd425dfc464dacdbd648a108aad5
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315458B2

Reaction notes

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