2-(2-Iodoethyl)indane → 5-Chloro-1-[1-[2-(indan-2-yl)ethyl]-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole

HRID 1267162

Reaction equation

HRID 1267162 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)[CH:6]=[CH:5]2.I[CH2:18][CH2:19][CH:20]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1>C(C(C)=O)C(C)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH2:16][CH2:15][N:14]([CH2:18][CH2:19][CH:20]3[CH2:21][C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:28]3)[CH2:13][CH:12]=1)[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 185458332-(2-Iodoethyl)indaneHCID 235048335-chloro-1-(pyridin-4-yl)-1H-indole

Product 1

HCID 185458365-Chloro-1-[1-[2-(indan-2-yl)ethyl]-1,2,3,6-tetrahydropyridin-4-yl]-1H-indoleYield 27%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5-chloro-1-(pyridin-4-yl)-1H-indole 26a (4.0 g), 2-(2-iodoethyl)indane 24a (4.8 g), and methyl isobutyl ketone (100 ml) was boiled under reflux for 20 h. The mixture was cooled, and a crystalline compound collected by filtration (6.5 g). Compound corresponding to 5.5 g was suspended in methanol (100 ml), and NaBH4 (1.5 g) was added in parts of 0.5 g. The resulting mixture was stirred at room temperature for 1 h, and the solvent was removed in vacuo. Conventional work up with ethyl acetate and water followed by purification on silica gel eluted with ethyl acetate-heptane (1:1) gave the crude product, which was crystallized (ethyl acetate) to give the title compound (1.1 g, 27%).

Workup

  1. temperatureunder reflux for 20 h
  2. temperatureThe mixture was cooled
  3. filtrationa crystalline compound collected by filtration (6.5 g)
  4. additionNaBH4 (1.5 g) was added in parts of 0.5 g
  5. customthe solvent was removed in vacuo
  6. customConventional work up with ethyl acetate and water followed by purification on silica gel
  7. washeluted with ethyl acetate-heptane (1:1)
  8. customgave the crude product, which
  9. customwas crystallized (ethyl acetate)

Sources & evidence

ORD record
ord-0f6e224d023b44c993e8a43863ad8ce9
Source dataset
uspto-grants-2003_04
Patent number
US06552044B2

Linked notes

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