Cesium carbonate → (+/-)-2-(hydroxy(5-methoxy-7-methyl-1H-indol-4-yl)methyl)benzo[d]thiazole-6-carbonitrile

Participants

Reaction Steps

tert-Butyl 4-((6-cyanobenzo[d]thiazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (40 mg, 0.089 mmol) and Cs2CO3 (145 mg, 0.445 mmol) were mixed in THF (0.5 mL) and MeOH (0.5 mL), and stirred at 65° C. for 2 hours. NaBH4 (67 mg, 1.78 mmol) was added to the reaction mixture and stirred at rt for 1 hour to reduce the oxidative by-products. The reaction mixture was then concentrated dissolved in MeOH and purified with HPLC (HC-B) to provide the title compound. 1H NMR (400 MHz, CD3OD) δ ppm 8.45 (d, J=1.01 Hz, 1H) 7.92 (d, J=8.59 Hz, 1H) 7.73 (dd, J=8.59, 1.52 Hz, 1H) 7.15 (d, J=3.28 Hz, 1H) 6.62-6.88 (m, 2H) 6.42 (d, J=3.03 Hz, 1H) 3.82 (s, 3H) 2.50 (s, 3H). HRMS calcd. for C13H15N3O2S (M+H)+ 350.0958. found 350.096.

Provenance & Evidence