Benzene → HCID 178435414, compound

Temperature

60 °C

A mixture of 2-ethyl-4-hydroxythieno[2,3-b]pyridine-5-carboxylic acid (380 mg, 1.7 mmol) and DMF (0.13 ml, 1.7 mmol) in benzene (5 ml) was heated to 60° C. and to the reaction mixture was added thionyl chloride (0.15 ml, 2.1 mmol). The mixture was stirred at 60° C. for 3 hours and then allowed to cool with an ice bath. The precipitated product was collected by filtration and washed with benzene. The resulting precipitate (223 mg) was dissolved in a mixture of 2-methoxyethanol (0.3 ml) and CH2Cl2 (5 ml) and then triethyamine (0.7 ml) were added to the solution. The mixture was stirred for 30 minutes and poured into chloroform. The resulting mixture was washed with 1N hydrochloric acid, dried (MgSO4) and evaporated in vacuo. The resulting residue was purified by flash column chromatography on silica gel. The column was eluted with ethyl acetate/hexane/chloroform (1:1:1) and then chloroform/methanol (9:1) to give 200 mg (41%) of the title compound as colorless powders.

1. temperatureto cool with an ice bath
2. filtrationThe precipitated product was collected by filtration
3. washwashed with benzene
4. dissolutionThe resulting precipitate (223 mg) was dissolved in a mixture of 2-methoxyethanol (0.3 ml) and CH2Cl2 (5 ml)
5. additiontriethyamine (0.7 ml) were added to the solution
6. stirringThe mixture was stirred for 30 minutes
7. additionpoured into chloroform
8. washThe resulting mixture was washed with 1N hydrochloric acid
9. dry with materialdried (MgSO4)
10. customevaporated in vacuo
11. customThe resulting residue was purified by flash column chromatography on silica gel
12. washThe column was eluted with ethyl acetate/hexane/chloroform (1:1:1)

ORD record

ord-eb5586bfe1004aa680577818eb935fda

Source dataset

uspto-grants-1994_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05284661