Benzothiazole-6-carbonitrile → tert-Butyl 4-((6-cyanobenzo[d]thiazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

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Reaction Steps

To a solution of 6-cyanobenzothiazol (CAS #:58249-61-9) (54.60 mg, 0.341 mmol) in THF (1.06 mL), LDA in Heptane/THF/Ethylbenzene (205 uL, 0.409 mmol) was added at −78° C. After 20 mins, a solution of tert-butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 19-D) (79 mg, 0.273 mmol) in THF (1.68 mL) was added to the reaction mixture at −78° C. After stirring for 1.5 h, the reaction was quenched with MeOH, sat. aq. NH4Cl solution and brine. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, concentrated, and purified using FCC eluting with Heptane/EtOAc to provide the title compound. MS (ESI−) m/z 448 (M−H).

Provenance & Evidence