Sodium Carbonate → 5-(1-Methyl-1H-pyrazol-4-YL)-1H-pyrrolo[2,3-B]pyridine

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Reaction Conditions

Reaction Steps

25 g of 5-bromo-1H-pyrrolo[2,3-b]pyridine 1 and 40 g of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole are dissolved 350 ml of DMF, and 20 g of tetrakis(triphenylphosphine)palladium are added under protective gas. After addition of 190 ml of 2N sodium carbonate solution, the batch is stirred at 100° C. for 12 h. All volatile constituents are removed in vacuo, and the residue is partitioned between ethyl acetate and water. Insoluble constituents are filtered off. After extraction of the aqueous phase, the combined organic phases are dried over sodium sulfate, filtered and evaporated to ¼ of the volume in vacuo. The crystal batch formed after 12 h at 0° C. is filtered off and combined with the first solid fraction, giving 22.7 g of compound 2; HPLC-MS: Rt=1.400 min; [M+H+]: 199.1.

Provenance & Evidence