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

HRID 656947ノート

反応式

HRID 656947 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5616d03f3b1249faafb55c1ab0461207
出典データセット
uspto-grants-2011_12
特許番号
US08071592B2

反応ノート

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