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

반응식

HRID 424845 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 104671Zinc trifluoromethanesulfonate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a3db19c76cf545ee94149b48c2b17fae
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106077B2

연결된 노트

불러오는 중…