تفاعل #88557

معادلة التفاعل

(S)-tert-butyl 1-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-4-yl)pyrrolidin-3-yl(ethyl)carbamate

Selectfluor

→

title compound

(S)-tert-butyl 1-(3-fluoro-6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-4-yl)pyrrolidin-3-yl(ethyl)carbamate

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىThe cooled reaction mixture
2. 2
   أخرىwas quenched with saturated aqueous sodium thiosulfate
3. 3
   workup.ADDITIONdiluted with ethyl acetate (50 mL)
4. 4
   غسيلwashed with water (20 mL)
5. 5
   أخرىThe organic layer was separated
6. 6
   تجفيفdried over sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىpurified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane)

الإجراء التجريبي

A mixture of (S)-tert-butyl 1-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-4-yl)pyrrolidin-3-yl(ethyl)carbamate (290 mg, 0.54 mmol) and Selectfluor™ (957 mg, 2.7 mmol) in acetonitrile (4.5 mL) was stirred at 0° C. for 5 minutes. The cooled reaction mixture was quenched with saturated aqueous sodium thiosulfate, diluted with ethyl acetate (50 mL), and washed with water (20 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane) to afford the title compound as a pale yellow foam, which was used in the next step without any further purification (120 mg).

المصدر