(4-Chloro-2-fluorophenyl)boronic acid → Methyl (2S)-tert-butoxy[4-(4-chloro-2-fluorophenyl)-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetate

Participants

Reaction Steps

The title compound was prepared from Methyl (2S)-tert-butoxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetate (Preparation 16, 100 mg, 212 μmol) and (4-chloro-2-fluorophenyl)boronic acid (74 mg, 424 μmol) using the same method as described in Example 44, Step 1 to yield 57 mg, 56%. Material obtained was a mixture of atropisomers, in a 3:1 ratio. 1H NMR (400 MHz, CDCl3) δ ppm 1.01 (s, 9H), 1.48-1.55 (m, 1H), 1.69-1.75 (m, 3H), 1.95-2.03 (m, 1H), 2.72 (s, 3H), 2.80-2.86 (m, 3H), 3.66 (s, 3H), 4.98 (s, 1H), 7.19-7.21 (m, 1H), 7.25-7.27 (m, 1H), 7.35-7.37 (m, 1H).

Provenance & Evidence