Triethylamine → 4-(4-Chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-1,3-dihydro-indol-2-one

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Reaction Steps

4-amino-oxindole (2.75 g, 18.6 mmol) was added portionwise to a solution of 5-trifluoromethyl-2,4-dichloropyrimidine (4.03 g, 1 eq) and ZnCl2 (18.6 mL of a 1M solution in ether) in 1:1 DCE/t-butanol (60 mL) at 0° C. After 15 minutes a solution of Et3N (2.85 mL, 1.1 eq) in 1:1 DCE/t-butanol (20 mL) was added dropwise. The reaction was allowed to warm to RT overnight. The reaction was then concentrated and the product triturated from methanol as a grey solid 3.05 g (50%). 1H NMR (DMSO-d6, 400 MHz) δ 3.43 (s, 2H), 6.64 (m, 1H), 7.14 (m, 2H), 8.74 (s, 1H), 10.32 (s, 1H), 10.43 (s, 1H); HPLC ret. time: 5.859 min. LRMS (M+) 329.1, 331.0.

Provenance & Evidence