Sodium hydride → methyl 4'-[(3,5-dibutyl-1H-1,2,4-triazol-1-yl)methyl][1,1'-biphenyl]-2-carboxylate

HRID 1587431ノート

反応式

HRID 1587431 の反応式
[CH2:1]([C:5]1[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[NH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[H][H].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([O:34][CH3:35])=[O:33])=[CH:22][CH:21]=1>CN(C)C=O.CO>[CH2:1]([C:5]1[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[C:27]([C:32]([O:34][CH3:35])=[O:33])=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:22][CH:21]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 149557953,5-Dibutyl-1H-1,2,4-triazoleHCID 178418361HCID 178418361、化合物

生成物 1

HCID 10319113methyl 4'-[(3,5-dibutyl-1H-1,2,4-triazol-1-yl)methyl][1,1'-biphenyl]-2-carboxylate収率 41%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

Under a static nitrogen atmosphere, 2.01 g (11.0 mmol) of solid 3,5-dibutyl-1H-1,2,4-triazole was added in small portions to 12 mmol of sodium hydride in 50 ml of dimethylformamide (DMF); stirring was continued until hydrogen evolution had ceased. The anion solution was cooled to -10° C. (ice/methanol) and treated with a solution of 3.37 g (11.0 mmol) of 4-bromomethyl-2'-methoxycarbonyl-biphenyl in 20 ml of dry DMF. The reaction was allowed to warm to ambient temperature and stir overnight. Methanol (10 ml) was added to destroy any unreacted sodium hydride and the DMF was removed in vacuo. The residue was dissolved in ethyl acetate, washed with water, and dried (MgSO4). Silica gel chromatography (Waters Prep-500A) using 40% ethyl acetate/hexane gave 2.0 g (41%) of compound as an oil: NMR (CDCl3) δ0.90 (t, J=7 HZ, 3H), 0.94 (t, J=7 Hz, 3H), 1.28-1.47 (m, 4H), 1.62-1.80 (m, 4H), 2.63-2.75 (m, 4H), 3.63 (s, 3H), 5.27 (s, 2H), 7.13-7.18 (m, 2H), 7.25-7.35 (m, 3H), 7.37-7.44 (m, 1H), 7.48-7.55 (m, 1H), 7.80-7.85 (m, 1H).

後処理

  1. stirringstir overnight
  2. customto destroy any unreacted sodium hydride
  3. customthe DMF was removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried (MgSO4)

出典と根拠

ORDレコード
ord-3efa0115ba4940fe9096a80d254e6495
出典データセット
uspto-grants-1993_06
特許番号
US05217985

反応ノート

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