Dimethylformamide → HCID 136141615, compound

Participants

Reaction Conditions

Reaction Steps

In a manner analogous to that of Example 184, 2.0 M aqueous Na2CO3 (0.66 mL) was added to a mixture of Intermediate 206(a) of Example 206 (1 g, 3.17 mmol), 4-(4,4,5,5-tetramethyl-[1,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1.18 g, 3.82 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.13 g, 0.159 mmol) in anhydrous N,N-dimethylformamide (50 ml), and the reaction was heated at 80° C. for 16 hours. When the reaction was judged complete, the volatile components were removed in vacuo. Ethyl acetate (50 mL), methanol (5 mL) and H2O (500 mL) were added, and the aqueous layer was extracted with ethyl acetate (3×20 mL). The combined ethyl acetate extracts were washed with H2O (2×50 mL) and brine (50 mL) and allowed to dry over Na2SO4. Following filtration, the volatile components were removed in vacuo and CH2Cl2 was added to the residue. The resulting solid was collected by filtration and washed with CH2Cl2 and diethyl ether to afford Intermediate 220(a) (1 g, 2.62 mmol) as a red solid in 82% yield.

Provenance & Evidence