Nicotinic Acid → 7-[(Pyridine-3-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 1986651Notes

Reaction equation

HRID 1986651 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.CCN(CC)CC.[CH3:17][O:18][C:19]([C:21]1[S:25][C:24]2[C:26]([NH2:30])=[CH:27][CH:28]=[CH:29][C:23]=2[CH:22]=1)=[O:20]>C(Cl)Cl>[CH3:17][O:18][C:19]([C:21]1[S:25][C:24]2[C:26]([NH:30][C:1]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)=[O:9])=[CH:27][CH:28]=[CH:29][C:23]=2[CH:22]=1)=[O:20]

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 45089769Methyl 7-amino-1-benzothiophene-2-carboxylate

Product 1

HCID 577224647-[(Pyridine-3-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl esterYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Nicotinic acid (401 mg, 3.26 mmol) was suspended in 20 mL CH2Cl2 and Et3N (330 mg, 3.26 mmol, 245 uL) was added to give a colorless solution. BopCl (829 mg, 3.26 mmol) was added and the reaction was stirred at room temperature for about 15 min, then a solution of 7-amino-benzo[b]thiophene-2-carboxylic acid methyl ester (450 mg, 2.17 mmol) in 2 mL CH2Cl2 was added. The yellow solution was stirred at room temperature for 12 h. After this time, room temperature, the solvent was removed from the reaction and the residue was partitioned between EtOAc (100 mL) and water (75 mL). The layers were separated and the organic portion was washed with water (2×75 mL), brine (75 mL), dried (MgSO4), filtered and the solvent was removed in vacuo to afford 7-[(pyridine-3-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester as a yellow solid (460 mg, 45%).

Workup

  1. customto give a colorless solution
  2. additionBopCl (829 mg, 3.26 mmol) was added
  3. stirringThe yellow solution was stirred at room temperature for 12 h
  4. customAfter this time, room temperature, the solvent was removed from the reaction
  5. customthe residue was partitioned between EtOAc (100 mL) and water (75 mL)
  6. customThe layers were separated
  7. washthe organic portion was washed with water (2×75 mL), brine (75 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-41058079585240909118317ecdde5cb4
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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