Methanesulfonyl chloride → 2-(chloro(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methyl)-4-phenyl-1-trityl-1H-imidazole
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:43][CH:44]([CH3:46])[CH3:45])[C:7]([F:42])=[C:8]([CH:10]([C:12]2[N:13]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=2)O)[CH:9]=1)[CH3:2].CS([Cl:51])(=O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[Cl:51][CH:10]([C:8]1[CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=[C:6]([O:43][CH:44]([CH3:46])[CH3:45])[C:7]=1[F:42])[C:12]1[N:13]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:16]=1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of Intermediate 25.1 (100 mg, 0.163 mmol) in 2 mL CH2Cl2, were added DMAP (2 mg, cat.), TEA (27 μL, 0.20 mmol) and MsCl (15.2 μL, 0.196 mmol). The mixture was stirred at rt for 30 min, then TEA (27 μL, 0.20 mmol) and MsCl (15.2 μL, 0.196 mmol) were added. The mixture was stirred at rt for 30 min, then was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4) and concentrated. to afford 125 mg of Intermediate 25.2 as a yellow solid, which was used in the following step without further purification.
Workup
- stirringThe mixture was stirred at rt for 30 min
- washwashed with H2O and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-af4f2bb0a4604ea5bf3dd15e8b88d870
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576098B2
Reaction notes
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