Water → 7-Fluoro-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-one

HRID 656947노트

반응식

HRID 656947 반응식
[F:1][C:2]1[CH:12]=[N:11][C:5]2[N:6]=[CH:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](I)[CH:20]=[CH2:21].O>CN(C=O)C>[F:1][C:2]1[CH:12]=[N:11][C:5]2[N:6]=[CH:7][C:8](=[O:10])[N:9]([CH2:21][CH:20]=[CH2:19])[C:4]=2[CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 594373427-Fluoropyrido[2,3-b]pyrazin-2(1H)-one

생성물 1

HCID 689911287-Fluoro-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-one수율 47%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

7-Fluoropyrido[2,3-b]pyrazin-2(1H)-one (306 mg, 1.855 mmol) was suspended in dry DMF (10 mL) under argon at rt, and the stirred suspension was treated with K2CO3 (845 mg, 6.12 mmol) and allyl iodide (223 μl, 2.41 mmol). It was then stirred for 1 h before addition of water (100 ml). The mixture was then extracted with DCM (2×200 ml) and 5% MeOH/DCM (100 ml). The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated and purified by column chromatography on silica with a 0-10% MeOH in DCM gradient to give the desired product as a yellow solid (177 mg, 47%).

후처리

  1. extractionThe mixture was then extracted with DCM (2×200 ml) and 5% MeOH/DCM (100 ml)
  2. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by column chromatography on silica with a 0-10% MeOH in DCM gradient

출처 및 근거

ORD 기록
ord-5616d03f3b1249faafb55c1ab0461207
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071592B2

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