Dimethylformamide → HCID 68286493, compound

Temperature

-5 °C

To a solution of Ethyl 4-amino-3,5-dibromothiophene-2-carboxylate (compound 34b, 5.0 g, 15.19 mmol) in DMF (25 ml) was added NaH (60% suspension in mineral oil) (1.82 g, 45.49 mmol) in portion wise manner at a temperature of about −5° C. The reaction mixture was then stirred at −5° C. for 20 min. To the reaction mixture was then added iodomethane (6.47 g, 2.83 ml, 45.59 mmol) and stirring was continued for 40 min at −5° C. The progress of the reaction was monitored by TLC. The reaction mixture was then quenched by addition of cold water (50 ml). the mixture so obtained was then extracted with ethyl acetate (3×100 ml). The combined organic layer was then dried over sodium sulphate and concentrated under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using 2.5% ethyl acetate in hexanes as an eluent to obtain the title compound (3.2 g, 58.97%).

1. waitwas continued for 40 min at −5° C
2. customThe reaction mixture was then quenched by addition of cold water (50 ml)
3. customthe mixture so obtained
4. extractionwas then extracted with ethyl acetate (3×100 ml)
5. dry with materialThe combined organic layer was then dried over sodium sulphate
6. concentrationconcentrated under reduced pressure
7. customto obtain a crude product, which
8. customwas then purified by flash column chromatography

ORD record

ord-e5b90abd806045ec91ad9166b3e7f173

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09393247B2