4-BROMOTHIENO[2,3-C]PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER

3, 5-Dibromoisonicotinaldehyde (80 g, 303 mmol), followed by cesium carbonate (98 g, 302 mmol) was added to a 2 L round bottom flask containing THF (1.3 L) under N2. Methyl mercaptoacetate (32 g, 302 mmol) was added and the mixture was heated at 60 °C overnight. After cooling to rt, ethyl acetate was added and the organic layer was washed with water, aqueous saturated NaHCO3, solution, and brine, then dried over and filtered to give a white solid The crude product was purified by recrystallization from ethyl acetate to give the desired product (60 g, 73percent).3, 5-Dibromoisonicotinaldehyde (80 g, 303 mmol), followed by cesium carbonate (98 g, 302 mmol) was added to a 2 L round bottom flask containing THF (1.3 L) under Ni. Methyl mercaptoacetate (32 g, 302 mmol) was added and the mixture was heated at 60 °C overnight. After cooling to rt, ethyl acetate was added and the organic layer was washed with water, aqueous saturated NaHOO:, solution, and brine, then dried over and filtered to give a white solid The crude product was purified by recrystallization from ethyl acetate to give the desired product (60 g, 73percent).3, 5-Dibromoisonicotinaldehyde (80 g, 303 mmol), followed by cesium carbonate (98 g, 302 mmol) was added to a 2 L round bottom flask containing THF (1.3 L) under N2. Methyl mercaptoacetate (32 g, 302 mmol) was added and the mixture was heated at 60 °C overnight. After cooling to rt, ethyl acetate was added and the organic layer was washed with water, aqueous saturated NaHCO3, solution, and brine, then dried over and filtered to give a white solid The crude product was purified by recrystallization from ethyl acetate to give the desired product (60 g, 73percent).[0188] Step 2: Methyl 4-bromothieno [2, 3-cl pyridine-2-carboxylate. 3, 5- Dibromoisonicotinaldehyde (80 g, 303 mmol), followed by cesium carbonate (98 g, 302 mmol) was added to a 2 L round bottom flask containing THF (1.3 L) under N2. Methyl mercaptoacetate (32 g, 302 mmol) was added and the mixture was heated at 60 °C overnight. After cooling to rt, ethyl acetate was added and the organic layer was washed with water, aqueous saturated NaHCO3 solution, and brine, then dried over Na2504 and filtered to give a white solid. The crude product was purified by recrystallization from ethyl acetate to give the desired product (60 g, 73percent).0196] Step 2: Methyl 4-bromothienor2, 3-c]pyridine-2-carboxylate. 3, 5- Dibromoisonicotinaldehyde (80 g, 303 mmol), followed by cesium carbonate (98 g, 302 mmol) was added to a 2 L round bottom flask containing THF (1.3 L) under NB. 4-bromothieno[2, 3-c]pyridine-2-carboxylic acid, 364b Lithium hydroxide (2.640 g, 110.246 mmol) was added to a solution of 0196] Step 2: Methyl 4-bromothienor2, 3-c]pyridine-2-carboxylate. 3, 5- Dibromoisonicotinaldehyde (80 g, 303 mmol), followed by cesium carbonate (98 g, 302 mmol) was added to a 2 L round bottom flask containing THF (1.3 L) under N2. Methyl mercaptoacetate (32 g, 302 mmol) was added and the mixture was heated at 60 C overnight. After cooling to rt, ethyl acetate was added and the organic layer was washed with water, aqueous saturated NaHC03 solution, and brine, then dried over Na2S04 and filtered to give a white solid. The crude product was purified by recrystallization from ethyl acetate to give the desired product (60 g, 73%).

Molecular Weight:272.12
XLogP3:2.7
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:270.93026
Monoisotopic Mass:270.93026
Topological Polar Surface Area:67.4
Heavy Atom Count:14
Complexity:239
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes