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Part D:A solution of compound 226 (0.56 g, 2.45 mmol) in acetic acid (20 mL) was stirred at reflux for 2 hours, at which time LC-MS analysis indicated that the reaction was complete. The reaction mixture was concentrated under vacuum. Purification by column chromatography (SiO2, 5percent MeOH / DCM) afforded compound 227 as a red oil 0.55 g (90percent). 1H NMR (400 MHz, DMSO-d6) δ 7.82 (d, 1 H), 7.44 (1 H), 7.24 (dd, 1 H), 4.75 (m, 1 H), 2.54 (s, 3H), 1.51 (d, 6H).
Part D:A solution of compound 226 (0.56 g, 2.45 mmol) in acetic acid (20 mL) was stirred at reflux for 2 hours, at which time LC-MS analysis indicated that the reaction was complete. The reaction mixture was concentrated under vacuum. Purification by column chromatography (SiO2, 5% MeOH / DCM) afforded compound 227 as a red oil 0.55 g (90%). 1H NMR (400 MHz, DMSO-d6) delta 7.82 (d, 1 H), 7.44 (1 H), 7.24 (dd, 1 H), 4.75 (m, 1 H), 2.54 (s, 3H), 1.51 (d, 6H).
80.1%
for 2.0h;Reflux;
5-bromo-N-isopropylbenzene-1,2-diamine (2.6 g, 11.40 mmol) was added into 117 glacial acetic acid (40 mL), and the reaction was refluxed for 2 hrs. After cooling to room temperature, acetic acid was removed under reduce pressure, the pH of the residue was adjusted to about 7 with saturated solution of 52 sodium bicarbonate, extracted with dichloromethane (50×3), the organic layer was combined, washed with brine, dried over anhydrous sodium sulfate, the filtrate was concentrated under reduced pressure, and the filtrate was separated on column chromatography (eluant:dichloromethane/methanol (v/v)=20:1) to afford 2.31 g a brown-yellow solid, yield was 80.10%, LC-MS(APCI): m/z=253.1 (M+1).
1-isopropyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
58.6%
With potassium acetate; palladium diacetate; In dimethyl sulfoxide; at 100.0℃; for 2.0h;Inert atmosphere;
Under nitrogen protection, TCHP (460 mg) and Pd(Oac)2 (230 mg) were added into the mixture of 228 6-bromo-2-methyl-1-isopropyl-1H-benzo[d]imidazole (2.30 g, 9.10 mmol), 27 bis(pinacolato)diboron (3.50 g, 13.6 mmol) and 28 potassium acetate (2.70 g, 27.3 mmol) in anhydrous 29 DMSO (25 mL), and the reaction was reacted under nitrogen protection at 100 C. for 2 hrs. After cooling to room temperature, the reaction was quenched by adding 48 water, extracted with ethyl acetate (100 mL×3), the organic layer was combined, washed with brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the filtrate was separated on column chromatography (eluant:petroleum ether/ethyl acetate (v/v)=2:1), to afford 1.60 g of a brown-yellow solid, yield was 58.6%. LC-MS(APCI): m/z=301.2 (M+1).
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