Methyl iodide → HCID 71281843, compound

To solution of ethyl 2-bromo-6H-thieno[2,3-b]pyrrole-5-carboxylate (6.35 g, 23.16 mmol) in DMF (80 mL) at 0° C. was added NaH (60%, 1.54 g, 38.50 mmol) in portions. Reaction mixture was stirred at 0° C. for 15 min before MeI (2.90 mL, 46.58 mmol) was added. It was then allowed to warm to room temperature and was stirred 1.5 h. Reaction mixture was cooled to 0° C. and was quenched with solution of NH4Cl (aqueous saturated, 50 mL). It was then diluted with H2O (˜200 mL) and product was extracted with EtOAc (3×100 mL). Combined organics were washed with NaCl (aqueous saturated, 80 mL) and dried over Na2SO4. After concentration of the solvent residue was purified by column chromatography (EtOAc/hexanes, 0-10% gradient) to yield ethyl 2-bromo-6-methyl-6H-thieno[2,3-b]pyrrole-5-carboxylate (5.47 g) in 82% yield.

1. customReaction mixture
2. additionwas added
3. customReaction mixture
4. temperaturewas cooled to 0° C.
5. customwas quenched with solution of NH4Cl (aqueous saturated, 50 mL)
6. additionIt was then diluted with H2O (˜200 mL) and product
7. extractionwas extracted with EtOAc (3×100 mL)
8. washCombined organics were washed with NaCl (aqueous saturated, 80 mL)
9. dry with materialdried over Na2SO4
10. customAfter concentration of the solvent residue was purified by column chromatography (EtOAc/hexanes, 0-10% gradient)

ORD record

ord-8c6dced21d104a309d691c3bfc81395c

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409905B2