Sodium Sulfate → HCID 44195007, compound

Participants

Reaction Steps

To a solution of (3-{5-[6-(6-methyl-pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-pyridin-3-yl}-benzylamino)-acetic acid methyl ester (Example 131) (1 eq, 0.216 mmol, 100 mg) in THF (2.5 ml) at 0° C. is added LAH (1M in THF, 0.8 eq, 0.173 mmol, 0.173 ml). The resulting suspension is allowed to warm to r.t. and then stirred for 1 h at this temperature. After cooling to 0° C. sat. aqueous Na2SO4 solution is added, and the mixture is stirred for additional 30 min. The suspension is filtered and concentrated under reduced pressure. Addition of 4 M aqueous NaOH solution is followed by extraction with EtOAc. The organic layer is dried with MgSO4, filtered, and concentrated under reduced pressure. The crude product is recrystallized using EtOAc/MeCN to give the title compound; [M+H]+=436; 1H-NMR (400 MHz, CD3OD): δ 8.98 (d, 1H), 8.90 (d, 1H), 8.50 (t, 1H), 8.26 (s, 1H), 8.20 (d, 1H), 7.80-7.76 (m, 2H), 7.68 (d, 1H), 7.56 (d, 1H), 7.50 (t, 1H), 7.43 (d, 1H), 7.25 (d, 1H), 6.70 (d, 1H), 3.89 (s, 2H), 3.69 (t, 2H), 2.77 (t, 2H), 2.62 (s, 3H).

Provenance & Evidence