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

HRID 1261201Notes

Reaction equation

HRID 1261201 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): 8.68 (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-e8ff519e632f437e9f69dc8cb50d00f8
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

Loading…