Cesium carbonate → methyl 1-(4-chloro-2-fluorobenzyl)-6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

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Methyl 6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (300 mg, 1.070 mmol) (example 1 step F) was dissolved in N,N-dimethylformamide (DMF) (10.700 ml). Cesium carbonate (418 mg, 1.284 mmol) and 4-chloro-2-fluorobenzyl bromide (263 mg, 1.177 mmol) were added to the solution. The reaction was set to stir at 65° C. overnight. The reaction was worked up by adding a saturated aqueous solution of NH4Cl followed by EtOAc. The layers were separated and the organic fraction was washed with water and brine. The reaction was dried over sodium sulfate and concentrated. The crude oil was passed on silica (0-60% AcOEt/Hex) and methyl 1-(4-chloro-2-fluorobenzyl)-6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (250 mg, 0.591 mmol, 55.2% yield) was recovered as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.46-7.39 (m, J=8.0 Hz, 2 H), 7.35-7.26 (m, J=7.9 Hz, 2 H), 7.18 (d, J=3.5 Hz, 1 H), 7.15-7.08 (m, 2 H), 7.07-7.00 (m, 1 H), 6.43 (d, J=3.5 Hz, 1 H), 5.53 (s, 2 H), 3.67 (s, 3 H), 2.75 (s, 3 H), 2.44 (s, 3 H) LCMS (m/z) ES+=423.2 (M+1).

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