Hydrochloric Acid → 4-Fluorothieno[2,3-c]pyridine-2-carboxylic acid

HRID 389539Notes

Reaction equation

HRID 389539 reaction equation
[F:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[S:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:3]=12.O.[OH-].[Li+].CO.Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[S:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:3]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 58622586Methyl 4-fluorothieno[2,3-c]pyridine-2-carboxylate

Product 1

HCID 667607174-Fluorothieno[2,3-c]pyridine-2-carboxylic acidYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-fluorothieno[2,3-c]pyridine-2-carboxylate (0.942 g, 4.46 mmol) in THF (23 mL) was added a solution of lithium hydroxide monohydrate (0.384 g, 9.14 mmol) in water (23 mL). Methanol (2.8 mL) was then added until the solution was transparent. The reaction mixture stirred 2 h at room temperature. The reaction was then adjusted to pH ˜4 by addition of 2 N aqueous HCl, causing formation of a white precipitate. THF and methanol were removed by rotary evaporation, and then the residual solid was collected by vacuum filtration, washing with water (2×25 mL). The collected white solid was dried in an oven at 50° C. to afford 765 mg (87%) of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 14.15 (br. s., 1 H), 9.23 (s, 1 H), 8.54 (s, 1 H), 8.14 (s, 1 H); MS (ESI): 198.05 [M+H]+; HPLC tR=2.40 min (ZQ3, polar—4 min).

Workup

  1. customTHF and methanol were removed by rotary evaporation
  2. filtrationthe residual solid was collected by vacuum filtration
  3. washwashing with water (2×25 mL)
  4. customThe collected white solid was dried in an oven at 50° C.

Sources & evidence

ORD record
ord-515afba5190d44ad804f0a2605d7ad69
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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