Sodium Bicarbonate → 3-Tert-butyl-7-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

HRID 2047644ノート

反応式

HRID 2047644 の反応式
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[N:8][OH:9])[NH2:7])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[C:18]([C:22]1[N:26]2[CH2:27][CH2:28][CH:29]([C:31](OC)=O)[CH2:30][C:25]2=[N:24][N:23]=1)([CH3:21])([CH3:20])[CH3:19].C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:18]([C:22]1[N:26]2[CH2:27][CH2:28][CH:29]([C:31]3[O:9][N:8]=[C:6]([C:5]4[CH:10]=[CH:11][C:2]([F:1])=[CH:3][CH:4]=4)[N:7]=3)[CH2:30][C:25]2=[N:24][N:23]=1)([CH3:21])([CH3:19])[CH3:20]

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 5930004-Fluoro-n-hydroxybenzimidamideHCID 23665647Potassium tert-butoxideHCID 67300325Methyl 3-tert-butyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-7-carboxylate

生成物 1

HCID 673002453-Tert-butyl-7-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine収率 50.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Add 4-fluorobenzamidoxime (4.61 g, 29.93 mmol) to a 1M solution of potassium t-butoxide (27.6 mL, 27.63 mmol) in tetrahydrofuran. Add methyl 3-tert-butyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-7-carboxylate (6.07 g, 23.02 mmol) and stir overnight at room temperature. Dissolve the reaction in a 1:1 mixture of 50% saturated aqueous sodium bicarbonate and ethyl acetate. Separate layers and extract the aqueous layer with additional ethyl acetate. Wash the combined organic layers with brine, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure. Purify the resulting residue by flash chromatography (silica gel), eluting with first 25-100% ethyl acetate:hexane and then 5% methanol in ethyl acetate. Recrystallize from dichloromethane and hexane to afford the title compound as a white solid (3.96 g). Mass spectrum (m/z): 342 (M+1).

後処理

  1. dissolutionDissolve
  2. customthe reaction
  3. extractionSeparate layers and extract the aqueous layer with additional ethyl acetate
  4. washWash the combined organic layers with brine
  5. dry with materialdry over anhydrous sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the resulting residue by flash chromatography (silica gel)
  9. washeluting with first 25-100% ethyl acetate
  10. customRecrystallize from dichloromethane and hexane

出典と根拠

ORDレコード
ord-8570bbd20d274f2f8a5e3e50cabedfa7
出典データセット
uspto-grants-2013_11
特許番号
US08592590B2

反応ノート

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