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

HRID 500764Notes

Reaction equation

HRID 500764 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(pm): 8.68 (d, J=5.2 Hz, 1H), 8.47 (dd, J=2.8 and 10.4 Hz, 1H), 8.20 (m, 1H), 8.17 (s, 1H), 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-a0b8369d1bb04f79b97fd8ea4dd81717
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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