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

HRID 561520Notes

Reaction equation

HRID 561520 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:16]1[C:24]2[C:19](=[C:20]([CH2:26][S:27][CH3:28])[CH:21]=[C:22]([F:25])[CH:23]=2)[NH:18][CH:17]=1)[CH2:10][C:11](OCC)=[O:12].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:16]1[C:24]2[C:19](=[C:20]([CH2:26][S:27][CH3:28])[CH:21]=[C:22]([F:25])[CH:23]=2)[NH:18][CH:17]=1)[CH2:10][CH2:11][OH:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58392475Ethyl 3-(2,4-dichlorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

Product 1

HCID 583923053-(2,4-Dichlorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 1.48 g (3.36 mmol) of the compound from Example 39A in 20 ml of tetrahydrofuran was added dropwise to 11.8 ml (11.8 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 ethyl acetate, and the organic phase was dried over magnesium sulfate, filtered and concentrated. 1.32 g (99% of theory) of the title compound were obtained.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4588bf4a3bec4f11acb840fc856d7547
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…