Hydrochloric Acid → HCID 66759575, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-chlorothieno[2,3-c]pyridine (685 mg, 4.00 mmol), benzophenone imine (1.03 mL, 6.00 mmol), sodium tert-butoxide (595 mg, 6.00 mmol), Xantphos (358 mg, 0.600 mmol), tris(dibenzylideneacetone)dipalladium(0) (185 mg, 0.200 mmol) and toluene (40 mL) was heated at 120° C. under a nitrogen atmosphere for 3 h. After cooling, the reaction mixture was partitioned between EtOAc (50 mL) and water (50 mL). The aqueous layer was extracted with EtOAc (50 mL). The combined organic fractions were washed with water (30 mL) and brine (30 mL), dried over MgSO4, and concentrated in vacuo. The residue was dissolved in THF (80 mL) and treated with aqueous 2 N hydrochloric acid (8.0 mL, 16 mmol). After 1 h at RT, the reaction mixture was diluted with water (50 mL) and extracted with EtOAc (3×30 mL). The extracts were washed with water (2×30 mL) and brine (30 mL). The aqueous layer was treated with aqueous NaOH until the pH was >9 and then extracted with EtOAc (3×50 mL). The combined organic extracts were washed with brine (30 mL), dried over MgSO4, and concentrated in vacuo. The resultant solid was purified by ISCO chromatography (50% to 100% EtOAc:heptane) to afford 420 mg (70%) of the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.64 (s, 1 H), 7.59 (d, J=5.6 Hz, 1 H), 7.12 (d, J=5.6 Hz, 1 H), 6.88 (d, J=1.2 Hz, 1 H), 4.36 (br s, 2 H); MS (ESI): 151.03 [M+H]+; HPLC tR=0.43 min (TOF: polar—3 min).

Provenance & Evidence