Potassium Hydroxide → 7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxylic acid

HRID 1710902Notes

Reaction equation

HRID 1710902 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]([O:16]C)=[O:15])[S:13][C:6]=12.[OH-].[K+]>C1COCC1>[F:1][C:2]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]([OH:16])=[O:15])[S:13][C:6]=12

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59424450Methyl 7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxylate

Product 1

HCID 594245367-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 38 (2.5 g, 7.18 mmol) in THF (50 ml) was added KOH (14.3 ml, 1.0 N in H2O, 14.3 mmol). After 4 hours the reaction mixture was concentrated and the resultant residue was dissolved in H2O (50 ml). The aqueous layer was then washed with ethyl acetate and acidified with 1N HCl (pH=1). The precipitate that formed upon acidification was collected by filtration, washed with water and dried under high vacuum to afford title compound 39 (2.3 g, 96% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.6 (d, J=5.2 Hz, 1H), 8.47 (dd, J=2.8 and 10.4 Hz, 1H), 8.20 (m, 1H), 8.17 (s, 1), 7.76 (dd, J=8.0 and 8.8 Hz, 1H), 7.04 (d, J=5.2 Hz, 1H).

Workup

  1. concentrationAfter 4 hours the reaction mixture was concentrated
  2. dissolutionthe resultant residue was dissolved in H2O (50 ml)
  3. washThe aqueous layer was then washed with ethyl acetate
  4. customThe precipitate that formed upon acidification
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-f479d5f128c64a0ca8392c8c386ce1e6
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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