Sodium Hydroxide → HCID 24874863, compound

Participants

Reaction Steps

Aqueous sodium hydroxide (2.0 M, 0.559 ml, 1.12 mmol) was added to a solution of 3-(3-amino-1-(2,6-dichloropyridin-4-yl)-1H-isoindol-1-yl)phenol (Scheme #19, D, 0.069 g, 0.19 mmol) in tetrahydrofuran (1 mL) at 0° C. 5-Chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl chloride (0.051 g, 0.22 mmol) was then added to the reaction mixture. After 30 minutes the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. Purification by flash chromatography using ethyl acetate followed by purification using preparative HPLC afforded 0.029 g (28% yield) of the title compound. 1H NMR (DMSO-d6) δ 7.87-7.77 (m, 2 H), 7.56-7.48 (m, 2 H), 7.41-7.34 (m, 2 H), 7.29 (s, 2 H), 7.12-7.01 (m, 3 H), 6.91 (d, J=1.77 Hz, 1 H), 3.74 (s, 3 H), 1.89 (s, 3 H); MS (AP) m/z 562 [M+1]+.

Provenance & Evidence