反应 #554680

反应方程式

tetrabutylammonium fluoride trihydrate

2-[2-(4-Isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazin-7-yl]ethynyl-trimethyl-silane

tetrabutylammonium fluoride trihydrate

→

sub-title compound

收率 61.0%

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

收率 61.0%

溶剂

THF

反应条件

后处理

1. 1
   温度the reaction mixture warmed to 40° C. for 6 hours
2. 2
   温度The reaction was cooled to ambient temperature
3. 3
   其他the layers separated
4. 4
   洗涤The organic layer was washed with 2M NaOH (×2), brine (×1)
5. 5
   干燥dried (MgSO4)
6. 6
   过滤filtered
7. 7
   浓缩concentrated in vacuo
8. 8
   其他The residue was purified by column silica gel chromatography
9. 9
   洗涤eluting with 15-20% EtOAc/DCM

实验过程

2-[2-(4-Isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazin-7-yl]ethynyl-trimethyl-silane (248 mg, 0.4495 mmol) in THF (5 mL) was treated with 1M tetrabutylammonium fluoride trihydrate (674.3 μL, 0.6743 mmol) and the reaction mixture allowed to stir at ambient temperature for 16 hours. A further portion of 1M tetrabutylammonium fluoride trihydrate (449.5 μL, 0.4495 mmol) was added and the reaction mixture warmed to 40° C. for 6 hours. The reaction was cooled to ambient temperature and added dropwise to a mixture of EtOAc/ice water and the layers separated. The organic layer was washed with 2M NaOH (×2), brine (×1), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column silica gel chromatography eluting with 15-20% EtOAc/DCM to give the sub-title compound as colourless crystals (89 mg, 61% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.20 (d, 6H), 3.40-3.50 (m, 1H), 4.20 (s, 1H), 8.00 (d, 2H), 8.33 (s, 1H), 8.44 (d, 2H), 9.06 (s, 1H) and 12.70 (s, 1H) ppm; MS (ES+) 326.0.

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