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Hydrochloric Acid → 3-(4-Chloro-2-fluorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

HRID 561518
Notes
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Reaction equation

HRID 561518 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])=[C:4]([F:28])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[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][CH2:10][OH:11])=[C:4]([F:28])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58392489Ethyl 3-(4-chloro-2-fluorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

Product 1

HCID 583923253-(4-Chloro-2-fluorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
3×

Procedure

A solution of 1.1 g (2.57 mmol) of the compound from Example 37A in 20 ml of tetrahydrofuran was added dropwise to 9.0 ml (9.0 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran in 50 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 715 mg (73% of theory) of the title compound.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. 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-30692b60524141eebed42c47e484d7bb
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063234B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes