Benzyl Bromide → (S)-ethyl 2-(2-(1-benzyl-3-methyl-1H-indazol-5-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-methyl-1H-indazol-5-yl)benzo[d]thiazol-6-yl)acetate (219 mg, 0.4 mmol) in ACN (5 mL) was added K2CO3 (166 mg, 1.2 mmol) and benzyl bromide (71 μL, 0.6 mmol). The reaction was then heated to 75° C. for 27 hours. After cooling to room temperature, the solids were filtered off, the crude reaction was concentrated and purified by column chromatography (gradient 0 to 20% EtOAc in hexanes) to give (S)-ethyl 2-(2-(1-benzyl-3-methyl-1H-indazol-5-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate. 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 1H), 8.05 (d, J=8.9 Hz, 1H), 7.92 (s, 1H), 7.60-7.45 (m, 4H), 7.35-7.27 (m, 4H), 7.22-7.18 (m, 2H), 5.54 (s, 2H), 5.16 (s, 1H), 4.21 (dtt, J=10.9, 7.4, 3.7 Hz, 2H), 2.63 (s, 3H), 2.60 (s, 3H), 1.26 (t, J=7.1 Hz, 3H), 0.98 (s, 9H).

Provenance & Evidence