Triethylamine → 2-(2-Fluoropyridin-4-ylmethylthio)pyridine-3-carboxylic acid

HRID 1984700Notes

Reaction equation

HRID 1984700 reaction equation
C(N(CC)CC)C.Cl[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([F:16])[CH:11]=1.[SH:17][C:18]1[N:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21].C(OCC)(=O)C>CN(C)C=O>[F:16][C:12]1[CH:11]=[C:10]([CH2:9][S:17][C:18]2[C:19]([C:20]([OH:22])=[O:21])=[CH:23][CH:24]=[CH:25][N:26]=2)[CH:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 108445134-(Chloromethyl)-2-fluoropyridineHCID 178524460HCID 178524460, compound

Product 1

HCID 230940282-(2-Fluoropyridin-4-ylmethylthio)pyridine-3-carboxylic acidYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of triethylamine (7.0 mL, 50 mmol) in N,N-dimethylformamide (20 mL) was added to a solution of 4-chloromethyl-2-fluoropyridine (Reference compound No. 1-1, 5.5 g, 38 mmol) and 2-mercaptonicotinic acid (6.2 g, 40 mmol) in N,N-dimethylformamide (40 mL) under ice-cooling, then the mixture was stirred for 12 hours at room temperature. Ethyl acetate (50 mL) was added to the reaction mixture, the whole was extracted with 0.1 N aqueous sodium hydroxide solution (100 mL). 1 N hydrochloric acid was added to the aqueous layer to adjust to pH 5, and the precipitated crystal was filtered off. The crystal was dried at 80° C. under reduced pressure to give 5.3 g of the title reference compound as a brown solid. (Yield 53%)

Workup

  1. extractionthe whole was extracted with 0.1 N aqueous sodium hydroxide solution (100 mL)
  2. addition1 N hydrochloric acid was added to the aqueous layer
  3. filtrationthe precipitated crystal was filtered off
  4. customThe crystal was dried at 80° C. under reduced pressure
  5. customto give 5.3 g of the title reference compound as a brown solid

Sources & evidence

ORD record
ord-8bfc315ed49242ea8f2cc19586117642
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

Loading…