Methyl 4-sulfanylbenzoate → 4-(1-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-1-methyl-ethylsulfanyl)-benzoic acid methyl ester

HRID 424830Notes

Reaction equation

HRID 424830 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22](O)([CH3:24])[CH3:23])=[C:18]([CH3:26])[CH:17]=2)=[C:12]([CH:27]([CH3:29])[CH3:28])[N:11]=[N:10]1.[SH:30][C:31]1[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=1>ClCCCl.[I-].[Zn+2].[I-]>[CH3:38][O:37][C:35](=[O:36])[C:34]1[CH:39]=[CH:40][C:31]([S:30][C:22]([C:19]2[CH:20]=[CH:21][C:16]([O:15][CH2:14][C:13]3[N:9]([C:3]4[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[N:10]=[N:11][C:12]=3[CH:27]([CH3:28])[CH3:29])=[CH:17][C:18]=2[CH3:26])([CH3:23])[CH3:24])=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 237573Methyl 4-sulfanylbenzoateHCID 667041762-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-propan-2-ol

Product 1

HCID 667041554-(1-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-1-methyl-ethylsulfanyl)-benzoic acid methyl esterYield 87%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

To an ambient temperature solution of 2-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-propan-2-ol (100 mg, 0.230 mmol) in DCE (1 mL) is added zinc iodide (37 mg, 0.115 mmol). The reaction is stirred at room temperature for 10 min. A solution of methyl 4-mercaptobenzoate (38 mg, 0.225 mmol) in DCE (1 mL) is added and the reaction is stirred overnight at room temperature. The reaction is concentrated under reduced pressure and the residue is chromatographed (SiO2 40 g, 0% to 30% EtOAC/Hexane to yield 4-(1-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-1-methyl-ethylsulfanyl)-benzoic acid methyl ester (114 mg, 87%). 1H NMR (400 MHz, CDCl3) δ 7.81 (d, 2H, J=7.9 Hz), 7.52-7.39 (m, 3H), 7.22 (s, 1H), 7.16 (d, 2H, J=7.8 Hz), 7.11 (d, 1H, J=8.4 Hz), 6.63 (d, 1H, J=8.4 Hz), 4.90 (s, 2H), 3.90 (s, 3H), 3.23 (sept, 1H, J=6.6 Hz), 2.01 (s, 3H), 1.64 (s, 6H), 1.46 (d, 6H, J=6.6 Hz).

Workup

  1. stirringthe reaction is stirred overnight at room temperature
  2. concentrationThe reaction is concentrated under reduced pressure
  3. customthe residue is chromatographed (SiO2 40 g, 0% to 30% EtOAC/Hexane

Sources & evidence

ORD record
ord-4d53d8db1d6f4eaaa5e42dadbc1569ec
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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