Dichloromethane → 3-[(2-Chloro-4-fluorophenyl)(cyclopropyl)methyl]-6-fluoro-7-[(methylsulfanyl)methyl]-1H-indole
Reaction equation
ClC1C=[C:6](F)[C:5]([CH:9]([CH:11]2[CH2:13][CH2:12]2)O)=[C:4](F)[CH:3]=1.F[C:16]([F:21])(F)[C:17](O)=O.[F:22][C:23]1[C:31]([CH2:32][S:33][CH3:34])=[C:30]2[C:26]([CH:27]=[CH:28][NH:29]2)=[CH:25][CH:24]=1.[Cl:35]CCl>>[Cl:35][C:4]1[CH:3]=[C:16]([F:21])[CH:17]=[CH:6][C:5]=1[CH:9]([CH:11]1[CH2:13][CH2:12]1)[C:27]1[C:26]2[C:30](=[C:31]([CH2:32][S:33][CH3:34])[C:23]([F:22])=[CH:24][CH:25]=2)[NH:29][CH:28]=1Participants
5
Reactant 4
Product 1
Procedure
514 mg (2.56 mmol) of the compound from Example 156A and 0.24 ml (3.07 mmol) of trifluoroacetic acid were added to 500 mg (2.56 mmol) of the compound from Example 9A in 4 ml of dichloromethane. The reaction mixture was stirred at RT for 30 min, and the crude product was then purified three times by preparative HPLC (mobile phase: acetonitrile/water gradient) and once by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10/1). 404 mg (41% of theory) of the title compound were obtained.
Workup
- customthe crude product was then purified three times by preparative HPLC (mobile phase: acetonitrile/water gradient)
Sources & evidence
- ORD record
- ord-4657a26252854f42966973f351de36ac
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063234B2
Reaction notes
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