Dimethylacetamide → HCID 71509514, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of compound 1 (Example 19, Step 2; 1.0 g, 3.03 mmol) in DMA (20 mL) were added Zn-powder (39.5 mg, 0.60 mmol), Zn(CN)2 (533 mg, 4.51 mmol) and xanthophos (630 mg, 1.12 mmol) at RT under N2 atmosphere. The reaction mixture was degassed with argon for 15 min and then Pd2(dba)3 (556 mg, 0.60 mmol) was added and again degassed for another 15 min. The resulting reaction mixture was heated to 110° C. and stirred for 12 h; progress of the reaction was monitored by TLC. The reaction mixture was cooled to RT; diluted with water (20 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude. The crude material was purified by silica gel column chromatography eluting with 70% EtOAc/Hexane to afford compound 2 (520 mg, 62%). 1H NMR (400 MHz, DMSO-d6): δ 10.34 (bs, 1H), 8.36 (s, 1H), 8.29 (d, J=8.0 Hz, 1H), 7.94 (d, J=7.6 Hz, 1H), 7.70 (t, J=7.6 Hz, 1H), 7.12 (d, J=8.4 Hz, 1H), 6.53-6.50 (m, 1H), 6.32 (d, J=2.4 Hz, 1H), 5.50 (s, 2H), 3.47 (s, 2H). MS (ESI): m/z 277 [M+1]+

Provenance & Evidence