Potassium Iodide → 2-Ethyl-6-fluoro-3-{1-[3-(4-fluorophenylsulfanyl)-propyl]-piperidin-4-YL}-1-phenyl-1H-indole

HRID 2356390Notes

Reaction equation

[CH2:1]([C:3]1[N:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]2[C:10]([C:11]=1[CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[CH:9][CH:8]=[C:7]([F:18])[CH:6]=2)[CH3:2].Br[CH2:26][CH2:27][CH2:28][S:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[CH2:1]([C:3]1[N:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]2[C:10]([C:11]=1[CH:12]1[CH2:13][CH2:14][N:15]([CH2:26][CH2:27][CH2:28][S:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[CH2:16][CH2:17]1)=[CH:9][CH:8]=[C:7]([F:18])[CH:6]=2)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-ethyl-6-fluoro-1-phenyl-3-piperidin-4-yl-1H-indole (70 mg, TFA salt), 1-(3-Bromo-propylsulfanyl)-4-fluoro-benzene (44 mg), potassium iodide (5 mg) and potassium carbonate (55 mg) in DMF (3 ml) is heated at 80° C. for 3 h, and allowed to cool to r.t. overnight. Ethyl acetate (50 ml) and water (25 ml) are added and the organic phase is washed with water, dried and concentrated in vacuo. The crude product is purified by flash chromatography (98:2 CH2Cl2:MeOH) to give 50 mg pure product (64%) as brown solid.

Workup

temperatureto cool to r.t. overnight
washthe organic phase is washed with water
customdried
concentrationconcentrated in vacuo
customThe crude product is purified by flash chromatography (98:2 CH2Cl2:MeOH)

Sources & evidence

ORD record: ord-f02b3860461d421696049fe42406db5c
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759365B2

Reaction notes

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