Sodium t-butoxide → HCID 178434953, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-2-(2-chloropyridin-3-yl)-2-hydroxypropanamide (0.094 g, 0.233 mmol), chloro-(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II)-methyl-tert-butyl ether adduct (Sigma Aldrich, 0.011 g, 0.014 mmol), sodium tert-butoxide (Aldrich, 0.045 g, 0.467 mmol) in Dioxane (0.933 ml) in a microwave vial was heated to 80° C. overnight. The reaction mixture was directly loaded onto a Biotage samplet. Purification by Biotage (25 g column; 0-100% EtOAc/hexane) followed by a second purification by Gilson HPLC (Gemini Gradient 10-70 method, Gemini-NX 10 u C18 column, 100×50 mm, solvets: ACN/0.1% TFA and water/0.1% TFA) to produce mixtures (R)-1-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-3-hydroxy-3-methyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one and (S)-1-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-3-hydroxy-3-methyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (0.0059 g, 0.016 mmol, 7% yield). M+1: 367.0. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.55 (s, 3 H) 2.53-2.72 (m, 2 H) 3.48-3.67 (m, 2 H) 4.63-4.77 (m, 1 H) 5.18-5.37 (m, 1 H) 7.03-7.18 (m, 1 H) 7.32-7.45 (m, 1 H) 7.46-7.61 (m, 2 H) 7.71-7.79 (m, 1 H) 7.79-7.88 (m, 1 H) 8.19-8.30 (m, 1 H).

Provenance & Evidence