Cesium carbonate → Methyl {5-[(5-{[(4-chlorophenyl)acetyl]amino}pyridin-3-yl)carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a stirred solution of 2-(4-chlorophenyl)-N-[5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylcarbonyl)pyridin-3-yl]acetamide (Example 308, 250 mg, 0.638 mmol) in DMF (4 mL) was added Cs2CO3 (374 mg, 1.15 mmol) followed by methyl bromoacetate (73 uL, 0.766 mmol). The reaction was stirred at 25° C. for 3 hours and then quenched with water (10 mL) and extracted with EtOAc (3×10 mL). The organics were combined, washed with water (10 mL) and saturated brine (10 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo to give a pale yellow oil (356 mg) which solidified on standing. Purification by column chromatography on silica gel (gradient of 0-100% 90:10:1 DCM/MeOH/NH3 in DCM) gave the title compound as a pale yellow solid in 70% yield, 208 mg. 1HNMR (400 MHz, CDCl3) δ 3.78 (s, 2H), 3.81 (s, 3H), 5.15 (s, 2H), 7.29-7.41 (m, 4H), 7.51 (s, 1H), 7.88 (s, 1H), 8.46 (m, 1H), 8.78-8.82 (m, 2H), 9.04 (s, 1H), 9.65 (s, 1H). LCMS (System 4): Rt=2.07 min; m/z 464 [M+H]+.

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