Trifluoroacetic anhydride → 2-Ethyl-6-iodo-3-methylimidazo[1,2-a]pyridine

HRID 2202986ノート

反応式

HRID 2202986 の反応式
[I:1][C:2]1[CH:3]=[CH:4][C:5](=[N:14]S(C2C=CC(C)=CC=2)(=O)=O)[N:6]([CH:8]([C:10](=O)[CH2:11][CH3:12])[CH3:9])[CH:7]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[CH2:11]([C:10]1[N:14]=[C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][N:6]2[C:8]=1[CH3:9])[CH3:12]

参加物

4

反応物 2

HCID 9845Trifluoroacetic anhydrideHCID 131735782N-(5-Iodo-1-(3-oxopentan-2-yl)pyridin-2(1H)-ylidene)-4-methylbenzenesulfonamide

生成物 1

HCID 231582522-Ethyl-6-iodo-3-methylimidazo[1,2-a]pyridine収率 52.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of N-(5-iodo-1-(3-oxopentan-2-yl)pyridin-2(1H)-ylidene)-4-methylbenzenesulfonamide (4 g) in THF (50 ml) was added trifluoroacetic anhydride (10 ml) at 0° C., and the resulting mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo, poured into saturated aqueous NaHCO3 solution and extracted with DCM. The extract was washed with brine, dried over Na2SO4, concentrated in vacuo, and purified by silica gel column chromatography (hexane/EtOAc) to afford the title compound (1.3 g) as a yellow solid.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionpoured into saturated aqueous NaHCO3 solution
  3. extractionextracted with DCM
  4. washThe extract was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel column chromatography (hexane/EtOAc)

出典と根拠

ORDレコード
ord-6432f6fd9d8748f19642b869821a16d5
出典データセット
uspto-grants-2016_06
特許番号
US09365540B2

反応ノート

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