Dichloromethane → HCID 58346437, compound

Participants

Reaction Steps

To 60 mL CH2Cl2 cooled to 0° C. was added 2-(6-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-2-yl)ethanol (1.60 g, 3.2 mmol), followed by thionyl bromide (2.31 g, 11.1 mmol). The contents were then stirred with warming to it over a 24 h period, after which time water (5 mL) was added to quench the reaction mixture. The solvent was removed under reduced pressure. The crude residue was diluted with aq. 2M Na2CO3 and vigorously stirred for 1 h. The precipitate was collected by filtration and triturated with methanol (30 mL) to afford the desired product (1.70 g, 94%) as a light-brown solid. 1H-NMR (DMSO-d6) δ 8.59 (d, 1H), 8.41 (s, 1H), 8.36 (s, 1H), 8.01 (s, 1H), 7.82 (dd, 1H), 7.78 (s, 1H), 7.47-7.60 (m, 2H), 7.30 (dd, 1H), 7.19 (d, 1H), 5.27 (s, 2H), 4.42 (t, 2H), 3.82 (t, 2H), 3.38 (t, 2H), 2.90 (t, 2H); LCMS RT=2.89 min; [M+H]+=567.4.

Provenance & Evidence