Water → 6-[5-(4-Hydroxy-tetrahydro-pyran-4-yl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide

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Reaction Conditions

Reaction Steps

To the crude 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (0.21 mmol, which is prepared according to the procedure for Step 3 of Example 16) is added 4-(5-bromo-pyridin-3-yl)-tetrahydro-pyran-4-ol (65.9 mg, 0.26 mmol), PdCl2(DPPF) (7.8 mg, 0.01 mmol) and Na2CO3 (45.1 mg, 0.43 mmol). 0.1 mL of H2O is added and the mixture is heated for 2 hrs at 80° C. The mixture is diluted with 50 mL EtOAc, quenched with 20 mL of saturated aqueous NH4Cl, washed with 2×20 mL of H2O and 1×20 mL of brine. The organic phase is dried with MgSO4, filtered and concentrated. The crude material is applied to a silica preparative TLC plate, and eluted (5% MeOH/CH2Cl2) to give 73 mg of 6-[5-(4-Hydroxy-tetrahydro-pyran-4-yl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide.

Provenance & Evidence