Reaction #156563

Reaction equation

water

NaH

2-(4-chloro-2-methoxypyridin-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

MeI

→

2-(4-Chloro-2-methoxypyridin-3-yl)-1-methylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Yield 65.4%

Solvents

DMF

Conditions

Workup

1. 1
   workup.STIRRINGThe resulted mixture was stirred for 6 h at rt
2. 2
   OtherThe brown precipitate was isolated
3. 3
   Washwashed with water
4. 4
   Otherdried under vacuum
5. 5
   OtherThe solid was purified by column chromatography (silica-gel, CH2Cl2/MeOH=49/1 v/v)
6. 6
   Otherto give a white solid product, 0.68 g, 65.4% yield

Procedure

NaH (0.12 g, 3.04 mmol) was added in portions to a solution of 2-(4-chloro-2-methoxypyridin-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione (1.0 g, 3.04 mmol) in 30 mL of anhydrous DMF at 0° C. under argon. The reaction mixture was then stirred at rt for 3 h. MeI (2.16 g, 15.2 mmol) was added dropwise via a syringe at rt under argon. The resulted mixture was stirred for 6 h at rt, hydrolyzed by adding 100 mL of water. The brown precipitate was isolated, washed with water and dried under vacuum. The solid was purified by column chromatography (silica-gel, CH2Cl2/MeOH=49/1 v/v) to give a white solid product, 0.68 g, 65.4% yield. MS: 343.0 [M−H]−. 1H NMR (DMSO-d6, 500 MHz): δ 11.27 (s, 1H), 8.42 (d, 1H, J=5.5 Hz), 8.23 (s, 1H), 8.08 (s, 1H), 7.43 (d, 1H, J=5.5 Hz), 3.89 (s, 3H), 3.75 (s, 3H).

Source