Diisobutylaluminumhydride → 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol

Participants

Reaction Steps

To a stirred solution of 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propionic acid ethyl ester (prepared as in Example 26, 300 mg, 0.6 mmol) in dry tetrahydrofuran (10 mL) at −78° C. was added diisobutylaluminum hydride (3.0 mL, 3.01 mmol). The mixture was then warmed to room temperature and stirred for 1 h. The reaction was quenched with a saturated aqueous potassium sodium tartrate solution at 0° C. After stirring at 0° C. for 30 min, the mixture was filtered and washed with tetrahydrofuran (100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol (236 mg, 86.1%) as a white solid: LC/MS m/e calcd for C25H32N2O4S [M+H]+ 457.61, observed 457.1; 1H NMR (400 MHz, CD3OD) δ ppm 7.87-7.92 (m, 3H), 7.59-7.64 (m, 3H), 6.36 (s, 1H), 4.31 (t, J=7.8 Hz, 1H), 3.56 (s, 2H), 3.10 (s, 3H), 2.25-2.34 (m, 1H), 2.07-2.15 (m, 1H), 1.62-1.89 (m, 6H), 1.45-1.57 (m, 2H), 1.02-1.42 (m, 6H).

Provenance & Evidence