tert-Butyl methyl ether → HCID 178429374, compound

Participants

Reaction Conditions

Reaction Steps

N-(Trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-2-(2-chloropyridin-3-yl)-2-methylpropanamide (0.086 g, 0.216 mmol), sodium t-butoxide (0.040 g, 0.416 mmol), and chloro(2-dicyclohexylphosphino-2′,6′-di-1-propoxy-1,1′-biphenyl)[2-(2-aminoethyl-phenyl)]palladium(ii), methyl t-butyl ether adduct (0.010 g, 0.012 mmol) were sealed in a microwave vessel under argon. Dry, sparged dioxane (0.5 mL) was added and the reaction heated at 80° C. After 35 minutes the mixture was cooled and partitioned between ethyl acetate (100 mL), water (100 mL) and saturated sodium bicarbonate (10 mL). The organic phase was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (dichloromethane to ethyl acetate gradient) followed by reverse phase HPLC gave 1-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (0.0481 g, 0.126 mmol, 58.6% yield) as an off white solid. M+1: 365.1. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.39 (s, 6 H) 2.45 (m, J=3.36 Hz, 2 H) 3.38-3.63 (m, 2 H) 4.51-4.72 (m, 1 H) 5.30 (quin, J=8.66 Hz, 1 H) 5.59-5.80 (m, 1 H) 6.97 (dd, J=7.16, 5.26 Hz, 1 H) 7.04-7.16 (m, 1 H) 7.21-7.35 (m, 1 H) 7.43 (dd, J=7.31, 1.61 Hz, 1 H) 7.59 (dd, J=10.52, 8.33 Hz, 2 H) 8.19 (dd, J=5.19, 1.53 Hz, 1 H).

Provenance & Evidence