반응 #170212
ord-e39f36dbb045417292916c9bd246c6b5
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후처리
- 1기타then partitioned between ethyl acetate (30 mL) and water (30 mL)
- 2기타The aqueous layer was separated
- 3추출finally extracted with ethyl acetate (2×50 mL)
- 4세척The combined organic phases were washed with a saturated solution of sodium chloride (3×50 mL)
- 5건조dried over sodium sulfate
- 6농축concentrated to dryness
- 7기타The residue was purified by chromatography on silica gel
실험 절차
3-(Thiophen-2-ylmethoxy)-azetidine hydrochloride (61 mg, 0.30 mmol), EDCI (71.5 mg, 0.37 mmol), HOBt (52 mg, 0.37 mmol) and diisopropylethylamine (110 μL, 0.62 mmol) were successively added to a solution of (E)-3-(3-((dimethylamino)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylic acid hydrochloride (70 mg, 0.25 mmol) in dimethylformamide (10 mL) at room temperature. The reaction mixture was stirred overnight then partitioned between ethyl acetate (30 mL) and water (30 mL). The aqueous layer was separated, basified with an aqueous solution of sodium hydroxyde (2N) until pH 12 and finally extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×50 mL), dried over sodium sulfate and concentrated to dryness. The residue was purified by chromatography on silica gel using dichloromethane/methanol/ammoniac (1:0:0.1 to 9:1:0.1) as eluent. The title product was obtained as a yellow solid (10 mg, 10%).