反应 #554681

反应方程式

tosyl chloride

sodium hydride

7-ethynyl-2-(4-isopropylsulfonylphenyl)-5H-pyrrolo[2,3-b]pyrazine

→

resultant precipitate

7-Ethynyl-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazine

溶剂

DMF

反应条件

后处理

1. 1
   其他reaction mixture
2. 2
   其他The reaction mixture was quenched by the slow addition of water (30 mL)
3. 3
   workup.STIRRINGthe mixture stirred for 20 minutes
4. 4
   萃取The aqueous layer was extracted with EtOAc (×3)
5. 5
   干燥the combined organic extracts dried (MgSO4)
6. 6
   过滤filtered
7. 7
   浓缩concentrated in vacuo
8. 8
   其他The residue was triturated form DCM/diethyl ether

实验过程

A 60% dispersion of sodium hydride in mineral oil (19.79 mg, 0.5164 mmol) was added slowly to a stirred solution of 7-ethynyl-2-(4-isopropylsulfonylphenyl)-5H-pyrrolo[2,3-b]pyrazine (140 mg, 0.4303 mmol) in DMF (1.2 mL) at 0° C. The reaction mixture was stirred at this temperature for 20 minutes then tosyl chloride (82.04 mg, 0.4303 mmol) was added and reaction mixture allowed to warm to ambient temperature over 16 hours. The reaction mixture was quenched by the slow addition of water (30 mL) and the mixture stirred for 20 minutes. The aqueous layer was extracted with EtOAc (×3) and the combined organic extracts dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated form DCM/diethyl ether and the resultant precipitate isolated by filtration to give the sub-tile compound as an off-white solid (112.6 mg, 59% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.19 (d, 6H), 2.37 (s, 3H), 3.45-3.50 (m, 1H), 4.55 (s, 1H), 7.49 (d, 2H), 8.01 (d, 2H), 8.08 (d, 2H), 8.41 (d, 2H), 8.75 (s, 1H) and 9.22 (s, 1H) ppm; MS (ES+) 480.0.

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