Imidazole → 2-Imidazol-1-yl-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carbonitrile

HRID 1268847ノート

反応式

HRID 1268847 の反応式
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([O-])([O-])=O.[Cs+].[Cs+].I[C:13]1[S:21][C:20]2[C:19]([C:22]#[N:23])=[CH:18][N:17]=[C:16]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:15]=2[CH:14]=1>[Cu]I.O1CCOCC1>[N:1]1([C:13]2[S:21][C:20]3[C:19]([C:22]#[N:23])=[CH:18][N:17]=[C:16]([NH:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)[C:15]=3[CH:14]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

参加物

6

反応物 3

HCID 795ImidazoleHCID 10796Cesium carbonateHCID 18446524HCID 18446524、化合物

生成物 1

HCID 184465232-Imidazol-1-yl-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carbonitrile収率 56.3%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

実験手順

To an oven dried Schlenk tube was added CuI (0.0057 g, 0.030 mmol), imidazole (0.097 g, 1.42 mmol), Cs2CO3 (0.405 g, 1.25 mmol). The tube was evacuated and purged to argon 5 times. Under argon, the tube was supplied with 2-iodo-4-(4-methoxybenzylamino)-thieno[3,2-c]pyridine-7-carbonitrile 27 (0.25 g, 0.59 mmol) trans-1,2-cyclohexanediamine (0.014 mL, 0.12 mmol), and dioxane (1 mL). The reaction contents were briefly evacuated and the vessel purged to argon 3 times, then sealed and brought to 110° C. with stirring. After 24 h, 20 mL of CH2Cl2 were added to the cooled reaction. The mixture was filtered and solvents removed in vacuo. Silica gel column chromatography (eluent: 3% MeOH in CH2Cl2) provided 0.12 g of 37. 1H NMR (400 MHz, d6-DMSO). δ 8.57 (t, J=6 Hz, 1H), 8.47 (s, 1H), 8.23 (bs, 1H), 8.00 (s, 1H), 7.71 (bs, 1H), 7.31 (d, J=8 Hz, 2H), 7.21 (bs, 1H), 6.91 (d, J=8 Hz, 2H), 3.74 (s, 3H).

後処理

  1. customTo an oven dried Schlenk tube
  2. customThe tube was evacuated
  3. custompurged to argon 5 times
  4. customThe reaction contents
  5. customwere briefly evacuated
  6. customthe vessel purged to argon 3 times
  7. customsealed
  8. custombrought to 110° C.
  9. addition20 mL of CH2Cl2 were added to the cooled reaction
  10. filtrationThe mixture was filtered
  11. customsolvents removed in vacuo

出典と根拠

ORDレコード
ord-195332380f8c4a65ad53e6b1944d0a6e
出典データセット
uspto-grants-2007_04
特許番号
US07199119B2

反応ノート

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