Hydrochloric Acid → 3-(4-Chlorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:25][S:26][CH3:27])[CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)[CH2:9][C:10](OCC)=[O:11])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:25][S:26][CH3:27])[CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)[CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1.29 g of the compound from Example 40A with a purity of 79% (2.52 mmol) in 30 ml of tetrahydrofuran was added dropwise to 11.1 ml (11.1 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran in 70 ml of tetrahydrofuran at RT under argon. The mixture was stirred at RT for 15 min and then 1N hydrochloric acid was added. The mixture was extracted with dichloromethane, and the organic phase was dried over magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 0.68 g (74% of theory) of the title compound.
Workup
- extractionThe mixture was extracted with dichloromethane
- dry with materialthe organic phase was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)
Sources & evidence
- ORD record
- ord-08c5f096a7004db3b915ad140f668197
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063234B2
Reaction notes
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