Chloride → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(1-methylpyrrol-2-yl)indole

HRID 1790494

Reaction equation

HRID 1790494 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20](Br)[CH:21]=4)[CH:16]=[CH:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:26][N:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[Sn](CCCC)(CCCC)CCCC.CN1C=CC=C1.[Cl-]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:28]5[N:27]([CH3:26])[CH:31]=[CH:30][CH:29]=5)[CH:21]=4)[CH:16]=[CH:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 73041-MethylpyrroleHCID 27693971-methyl-2-(tributylstannyl)-1H-pyrroleHCID 22038188HCID 22038188, compound

Product 1

HCID 220379511-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(1-methylpyrrol-2-yl)indoleYield 57.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-bromoindole (0.2 g) was dissolved in toluene (2.50 ml). Next, 1-methyl-2-tributylstannylpyrrole (1.44 g) synthesized in accordance with the method described in Tetrahedron Lett., 4407 (1986). with the use of 1-methylpyrrole and tributylthin chloride was added thereto and the resultant mixture was heated under reflux for 3 hr under nitrogen atmosphere. After adding ethyl acetate, the mixture was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (0.115 g) as a yellow oil (yield: 57.28%).

Workup

  1. temperatureunder reflux for 3 hr under nitrogen atmosphere
  2. washthe mixture was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-9dc8408c89a94e299be6d35e8736e5aa
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Linked notes

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