反应详情

To solution of methyl 5-ethyl-6-(5-formyl-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinate (49.4 mg, 0.14 mmol) in dichloroethane (1.5 mL) was added pyrrolidine (20 μL, 0.24 mmol) followed by AcOH (15 μL, 0.25 mmol). After stirring at room temperature for 10 min NaBH(OAc)3 (60 mg, 0.28 mmol) was added. Reaction was stirred at room temperature overnight and then quenched with NaHCO3 solution (aqueous saturated, 5 mL). Product was extracted with DCM (3×7 mL). Organic phase was dried over Na2SO4 and solvent was concentrated. Product was purified by column chromatography (MeOH/DCM, 0-5% gradient). Methyl 5-ethyl-2-methoxy-6-(6-methyl-5-(pyrrolidin-1-ylmethyl)-6H-thieno[2,3-b]pyrrol-2-yl)nicotinate (49.7 mg) was obtained in 86% yield. LC-MS 343.1 [M-71+H]+, RT 1.00 min.

1. additionwas added
2. customReaction
3. customquenched with NaHCO3 solution (aqueous saturated, 5 mL)
4. extractionProduct was extracted with DCM (3×7 mL)
5. dry with materialOrganic phase was dried over Na2SO4 and solvent
6. concentrationwas concentrated
7. customProduct was purified by column chromatography (MeOH/DCM, 0-5% gradient)