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To a solution of ethyl 6-chlorobenzothiophene-2-carboxylate Xl-9a (9.00 g, 37.5 mmol) inEtOH was added 3 N NaOH (24.9 ml, 74.7 mmol) and the reaction mixture was stirred at20 room temperature for 16h. Progress of the reaction was monitored by TLC. Aftercompletion, the reaction mixture was concentrated under vacuum. The residue wasdiluted with H20 (200 ml), acidified with 2 N HCI and extracted with EtOAc (2 x 300 ml).The organic layer was separated, dried over anhydrous Na2S04 and concentrated undervacuum to afford 6-chlorobenzothiophene-2-carboxylic acid Xl-9b (6.1 0 g) as an off-whitesolid.This compound was used as such for the next reaction without further purification.Yield: 77percent5 1H NMR (400 MHz, DMSO-d5) o 8.00 (d, J=8.31 Hz, 2H) 8.10 (s, 1 H) 8.21 (s, 1 H) 13.52(brs, 1 H).
With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 16h;
To a solution of 4- chloro--2--fluorobenzaldehyde (10.0 g, 63.0 mmol) in DMF (100 ml) wasadded ethyl thioglycolate (11.3 g, 94.6 mmol) followed by addition of K2C03 (26.1 g, 189mmol). The reaction mixture was heated at 70C for 16h. Progress of the reaction wasmonitored by TLC. After completion, the reaction mixture was diluted with H20 (300 ml)10 and extracted with EtOAc (2 x 300 ml). The organic layer was separated, dried overanhydrous Na2S04 and concentrated under vacuum to afford ethyl 6-chlorobenzothiophene-2-carboxylate Xl-9a (9.1 0 g) as an off-white solid.This compound was used as such for the next reaction without further purification.Yield: 60%15 1H NMR (400 MHz, DMSO-d5) o 1.33 (t, J=7.09 Hz, 3H) 4.35 (q, J=7.01 Hz, 2H) 7.51 (dd,J=8.56, 1.71 Hz, 1 H) 8.04 (d, J=8.80 Hz, 1 H) 8.20 (s, 1 H) 8.25 (d, J=0.98 Hz, 1 H).
With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 60℃; for 22.5h;
[000922] Compound 242A (2.44 g, 15.4 mmol) and potassium carbonate (2.76 g, 20.0 mmol) were suspended in dry DMF (15 mL) and the resulting mixture was cooled to 0 C. Ethyl thioglycolate (1.7 mL, 15.5 mmol) was added in portions over 1 h and the reaction mixture was warmed slowly to room temperature and stirred at 25 C for 16 h. The reaction was heated at 60 C for 5.5 h before cooling and adding water (30 mL). The resulting mixture was stirred at room temperature for 30 min and filtered. The residue was washed with water (5 mL x 2) and dried to afford the Compound 242B.
With ethanol; sodium hydroxide; at 20℃; for 16.0h;
To a solution of ethyl 6-chlorobenzothiophene-2-carboxylate Xl-9a (9.00 g, 37.5 mmol) inEtOH was added 3 N NaOH (24.9 ml, 74.7 mmol) and the reaction mixture was stirred at20 room temperature for 16h. Progress of the reaction was monitored by TLC. Aftercompletion, the reaction mixture was concentrated under vacuum. The residue wasdiluted with H20 (200 ml), acidified with 2 N HCI and extracted with EtOAc (2 x 300 ml).The organic layer was separated, dried over anhydrous Na2S04 and concentrated undervacuum to afford 6-chlorobenzothiophene-2-carboxylic acid Xl-9b (6.1 0 g) as an off-whitesolid.This compound was used as such for the next reaction without further purification.Yield: 77%5 1H NMR (400 MHz, DMSO-d5) o 8.00 (d, J=8.31 Hz, 2H) 8.10 (s, 1 H) 8.21 (s, 1 H) 13.52(brs, 1 H).
With water; potassium hydroxide; In ethanol; for 1.5h;Reflux;
[000923] Compound 242B (500 mg, 2.08 mmol) was dissolved in hot ethanol (12 mL) and a solution of potassium hydroxide (642 mg, 11.5 mmol) in water (12 mL) was added to the mixture. The suspension was heated at reflux for 1.5 h during which time it mostly dissolved. After cooling slightly aqueous HC1 solution (6 N, 5 mL) was added dropwise. Ethanol was evaporated in vacuo and the residual solid was filtered. The filtered cake was washed with water (20 mL) and dried to give Compound 242C.
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