Cesium carbonate → 5-(4-Methyl-1H-imidazol-1-yl)pyridin-2-amine

HRID 592177

反応式

HRID 592177 の反応式
I[C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:9][C:10]1[N:11]=[CH:12][NH:13][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I.CN(C=O)C>[CH3:9][C:10]1[N:11]=[CH:12][N:13]([C:2]2[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=2)[CH:14]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 885792-Pyridinamine, 5-iodo-HCID 178418800HCID 178418800、化合物

生成物 1

HCID 575128615-(4-Methyl-1H-imidazol-1-yl)pyridin-2-amine

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

To a seal tube charged with 5-iodopyridin-2-amine 143-1 (1.1 g, 5 mmol), 4-methyl-1H-imidazole 143-2 (0.61 g, 7.4 mmol), CuI (0.31 g, 1.63 mmol) and Cs2CO3 (3.25 g, 10 mmol) was added DMF (10 mL). The reaction vessel was flushed with nitrogen and sealed. The reaction was stirred at room temperature for 30 minutes before being heated up to 110° C. for 24 hours. The reaction was diluted into ethyl acetate and the salt was removed by filtration. The filtrate was dried and the residue was purified by silica gel flash chromatography, eluted with 10% methanol in ethyl acetate to give 5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine 143-3 as off-white solid. MS m/z 175.2 (M+1).

後処理

  1. customThe reaction vessel was flushed with nitrogen
  2. customsealed
  3. temperaturebefore being heated up to 110° C. for 24 hours
  4. additionThe reaction was diluted into ethyl acetate
  5. customthe salt was removed by filtration
  6. customThe filtrate was dried
  7. customthe residue was purified by silica gel flash chromatography
  8. washeluted with 10% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-11551f06a5e24d609b4fceb3ea4d0b6a
出典データセット
uspto-grants-2016_01
特許番号
US09238646B2

関連ノート

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