N,N'-Dimethylethylenediamine → 4-(cyclopropylsulfonyl)-1H-pyrazolo[3,4-b]pyridine

HRID 1802889ノート

反応式

HRID 1802889 の反応式
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.CNCCNC.[CH:17]1([S:20]([O-:22])=[O:21])[CH2:19][CH2:18]1.[Na+].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[CH:17]1([S:20]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[NH:8][N:9]=[CH:10][C:3]=23)(=[O:22])=[O:21])[CH2:19][CH2:18]1

参加物

7

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 42643363Sodium cyclopropanesulfinateHCID 576428014-Iodo-1H-pyrazolo[3,4-b]pyridine

生成物 1

HCID 579641094-(cyclopropylsulfonyl)-1H-pyrazolo[3,4-b]pyridine収率 9%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 4-iodo-1H-pyrazolo[3,4-b]pyridine (5.2 g) in dimethyl sulfoxide (70 mL) were added N,N′-dimethylethylenediamine (114 μL), copper (I) iodide (202 mg), sodium cyclopropanesulfinate (8.16 g) and potassium carbonate (5.06 g) at room temperature under argon atmosphere, and the mixture was stirred at 100° C. for 16 hr. The reaction mixture was filtered, water was added to the filtrate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (0.42 g, yield 9%) as yellow crystals from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 224 (MH+).

後処理

  1. filtrationThe reaction mixture was filtered
  2. additionwater was added to the filtrate
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-0a58d9542a994a4c8bc0e0482c449355
出典データセット
uspto-grants-2013_01
特許番号
US08349886B2

反応ノート

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