Triethylamine → 4-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenylethynyl}-benzoic acid methyl ester

HRID 424845

反応式

HRID 424845 の反応式
Br[C:2]1[CH:25]=[CH:24][C:5]([O:6][CH2:7][C:8]2[N:12]([C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:20])[N:11]=[N:10][C:9]=2[CH:21]([CH3:23])[CH3:22])=[CH:4][C:3]=1[CH3:26].[CH3:27][O:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][C:33]([C:36]#[CH:37])=[CH:32][CH:31]=1.C(N(CC)CC)C>CN(C=O)C.[O-]S(C(F)(F)F)(=O)=O.[Zn+2].[O-]S(C(F)(F)F)(=O)=O>[CH3:27][O:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][C:33]([C:36]#[C:37][C:2]2[CH:25]=[CH:24][C:5]([O:6][CH2:7][C:8]3[N:12]([C:13]4[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=4[Cl:20])[N:11]=[N:10][C:9]=3[CH:21]([CH3:22])[CH3:23])=[CH:4][C:3]=2[CH3:26])=[CH:32][CH:31]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 640163Methyl 4-ethynylbenzoateHCID 667040695-(4-Bromo-3-methyl-phenoxymethyl)-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-[1,2,3]triazole

生成物 1

HCID 667041244-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenylethynyl}-benzoic acid methyl ester収率 64.6%

試薬・触媒・溶媒 2

HCID 104671Zinc trifluoromethanesulfonate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a room temperature solution of 5-(4-bromo-3-methyl-phenoxymethyl)-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-[1,2,3]triazole (50 mg, 0.110 mmol) in DMF (1 mL) are added 4-ethynyl-benzoic acid methyl ester (18 mg, 0.110 mmol) and triethylamine (107 μL, 0.770 mmol). The reaction mixture is degassed for 20 minutes with nitrogen. To the reaction mixture are added dichloro(bistriphenylphosphine) palladium (II) (8 mg, 0.011 mmol, 10 mol %) and zinc (II) triflate (40 mg, 0.110 mmol). The reaction mixture is heated to 80° C. After 3 h, the reaction is concentrated and the residue is chromatographed (40 g SiO2, 0% to 5% EtOAc/Hexanes) to yield 4-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenylethynyl}-benzoic acid methyl ester (38 mg, 64%). LC/MS m/e 534.2 (M+1).

後処理

  1. customThe reaction mixture is degassed for 20 minutes with nitrogen
  2. concentrationthe reaction is concentrated
  3. customthe residue is chromatographed (40 g SiO2, 0% to 5% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-a3db19c76cf545ee94149b48c2b17fae
出典データセット
uspto-grants-2012_01
特許番号
US08106077B2

関連ノート

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