Methyl iodide → ethyl 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylate

HRID 2118118ノート

反応式

HRID 2118118 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:7]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-:3])=[O:2].IC.[C:26]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:26][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 741309ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate

生成物 1

HCID 69231753ethyl 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylate収率 105%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate (1.0 g, 3.23 mmol) and iodomethane (2.5 mL, 40.2 mmol) in DMF (25 mL) was treated with Cs2CO3 (3.26 g, 10 mmol) and stirred for 16 h. The reaction was quenched by addition of water and the solid was collected and dried to yield ethyl 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylate as a yellowish solid (1.1 g, 100%): 1H NMR (DMSO-d6) δ 1.03 (t, J=7.0 Hz, 3H, 4.09 (s, 3H, 4.18 (q, J=7.0 Hz, 2H, 7.40-7.55 (m, 5H, 7.90 (d, J=9.2 Hz, 1H, 8.23 (dd, J=9.2, 2.3 Hz, 1H, 8.32 (d, J=2.3 Hz, 1H; MS (EI) m/z 325.2 (MH+).

後処理

  1. customThe reaction was quenched by addition of water
  2. customthe solid was collected
  3. customdried

出典と根拠

ORDレコード
ord-a42accc70b634a13bdf0929eeea1041d
出典データセット
uspto-grants-2008_10
特許番号
US07442805B2

反応ノート

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