Water → 3-(4-Chlorophenyl)-3-{6-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

HRID 561527Notes

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])[C:20]([F:24])=[CH:21][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-].C(#N)C.O>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])[C:20]([F:24])=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2.33 g (5.7 mmol) of the compound from Example 47A in 18 ml of tetrahydrofuran was added dropwise to 20.1 ml (60.1 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran and 20 ml of tetrahydrofuran at RT. The mixture was stirred at 60° C. for 1 h, acetonitrile was added, and water was added to the solution while cooling in ice. The solid was filtered off with suction from the suspension, the filtrate was concentrated, and the residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 1.72 g (82% of theory) of the title compound were obtained.

Workup

temperaturewhile cooling in ice
filtrationThe solid was filtered off with suction from the suspension
concentrationthe filtrate was concentrated
customthe residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record: ord-1994f88aa1fd4d3287a15a240387ad6f
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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