Dimethyl Sulfoxide → 3-{1-[2-(1-benzothiophene-3-yl)ethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole

HRID 1768019Notes

Reaction equation

HRID 1768019 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH2:10][CH2:11]I)[C:6]=2[CH:13]=1.N1CC=C([N:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)CC1.C([N:32]([CH2:36][CH3:37])[CH:33]([CH3:35])C)(C)C.[CH3:38]S(C)=O>>[S:9]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:13][C:6]=2[C:7]([CH2:10][CH2:11][N:32]2[CH2:33][CH:35]=[C:38]([C:22]3[C:23]4[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=4)[NH:20][CH:21]=3)[CH2:37][CH2:36]2)=[CH:8]1

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 23001082(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indoleHCID 236144415-Chloro-3-(2-iodoethyl)-1-benzothiophene

Product 1

HCID 112336643-{1-[2-(1-benzothiophene-3-yl)ethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole

Procedure

A mixture of 2-(5-chloro-1-benzothiophene-3-yl)ethyl iodide (318 mg. 1 mmol) (obtained by the above mentioned process) and 3 (1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (198 mg, 1 mmol) was heated at 120° C. in DMSO in the presence of N,N-diisopropylethylamine (5 ml, excess) for 24 hrs. At the end, the reaction mixture was quenched with water and extracted with chloroform. The organic layer was washed with water and dried over anhydrous MgSO4 and concentrated to dryness. The dark colored solid was purified by silica-gel column chromatography by eluting it with 70% ethyl acetate:hexane. 3-{1-[2-(1-benzothiophene-3-yl)ethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole was isolated as yellow oil; Yield: 115 mg (29%); 393 (M+H); 1H-NMR: δ 8.10(1H, s, NH), 7.91(1H, d, J=8 Hz), 7.77(2H, m), 7.25(6H, m), 6.24(1H, s), 3,37(2H, d, J=3 Hz), 3.18(2H, t, J=7.7 Hz), 2.87(4H, m), 2.68(2H, s).

Workup

  1. customobtained by the
  2. customAt the end, the reaction mixture was quenched with water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated to dryness
  7. customThe dark colored solid was purified by silica-gel column chromatography
  8. washby eluting it with 70% ethyl acetate

Sources & evidence

ORD record
ord-bbff77031d474f3a8a7fb2e02242f78c
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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