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With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl acetamide; at 200℃; for 1h;Microwave irradiation;
To a solution of 6-chlorobenzothiophene-2-carboxylic acid Xl-9b (1.00 g, 4.70 mmol) inDMA (5 ml) was added DBU (2.86 g, 18.8 mmol) and reaction mixture was heated in10 microwave at 200C for 1 h. Progress of the reaction was monitored by TLC. Aftercompletion, the reaction mixture was diluted with H20 (30 ml) and extracted with EtOAc(3 x 20 ml). The organic layer was separated, dried over anhydrous Na2S04 andconcentrated under vacuum to afford 6-chlorobenzothiophene Xl-9 (0.51 g) as an offwhitesolid.15 This compound was used as such for the next reaction without further purification.20Yield: 65%1H NMR (400 MHz, DMSO-d5) o 7.41 (dd, J=8.56, 1.71 Hz, 1 H) 7.47 (d, J=5.38 Hz, 1 H)7.80 (d, J=5.38 Hz, 1 H) 7.89 (d, J=8.80 Hz, 1 H) 8.17 (d, J=0.98 Hz, 1 H).
With copper; In quinoline; at 182℃; for 2h;
[000924] Compound 242C (420 mg, 1.98 mmol) and copper powder (63 mg, 0.99 mmol) were suspended in quinoline (10 mL) and the resulting mixture was heated at 185 C for 2 h. After cooling down to room temperature, ethyl acetate (25 mL) was added and the suspension was filtered. The filtered cake was washed with ethyl acetate (5 mL x 2) and the combined organic layers were washed with aqueous HC1 solution (2 N, 10 mL x 2). After drying over anhydrous sodium sulfate, the solution was filtered and evaporated in vacuo to give a residue. The crude product was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 10% v/v) to afford Compound 242D.
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