2-ethyl-5-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole → 2-ethyl-5-fluoro-3-piperidin-4-yl-1H-indole

HRID 405913Notes

Reaction equation

HRID 405913 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[C:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH:17]=1)=[CH:9][C:8]([F:18])=[CH:7][CH:6]=2)[CH3:2]>CO.[Pd]>[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[CH:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1)=[CH:9][C:8]([F:18])=[CH:7][CH:6]=2)[CH3:2]

Participants

4

Reactant 1

HCID 666697172-ethyl-5-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 581176272-ethyl-5-fluoro-3-piperidin-4-yl-1H-indole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.83 g 2-ethyl-5-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole are suspended in 50 ml of methanol and hydrogenated with 0.3 g Pd/C 10% at normal pressure and ambient temperature. The catalyst is suction filtered and the filtrate is evaporated to dryness. 2.3 g (V-1) are obtained as a solid. 1H NMR (400 MHz, DMSO): 2.70 (2H, q); 1.19 (3H, t).

Workup

  1. filtrationfiltered
  2. customthe filtrate is evaporated to dryness
  3. custom2.3 g (V-1) are obtained as a solid

Sources & evidence

ORD record
ord-ffb8e08248034212a4c74cad44a40304
Source dataset
uspto-grants-2014_06
Patent number
US08754073B2

Reaction notes

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