反应详情

In a 100 mL round-bottomed flask, lithium 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (400 mg, 1.48 mmol, Eq: 1.00), ethanamine hydrochloride (145 mg, 1.78 mmol, Eq: 1.2) and HATU (675 mg, 1.78 mmol, Eq: 1.2) were combined in DMF (6 mL) to give a light yellow suspension. Triethylamine (0.45 mL, 3.2 mmol, Eq: 2.2) was added. The reaction was stirred overnight then diluted with ethyl acetate (30 mL) and saturated aqueous NaHCO3 (20 mL). The aqueous layer was separated, extracted with DCM (20 mL×2) and the combined organic layers were washed with 1 M aqueous NaOH (10 mL), dried over Na2SO4 and concentrated in vacuo. The residue was azeotroped with n-heptane (30 mL×3) to give tert-butyl 2-(ethylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (322 mg), m/z=292 (M+H).

1. customto give a light yellow suspension
2. customThe aqueous layer was separated
3. extractionextracted with DCM (20 mL×2)
4. washthe combined organic layers were washed with 1 M aqueous NaOH (10 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo
7. customThe residue was azeotroped with n-heptane (30 mL×3)