(E)-5-(2-(phenylsulfonyl)vinyl)-1H-indole → 3-Dealkyl eletriptan

HRID 473056Notes

Reaction equation

HRID 473056 reaction equation
[C:1]1([S:7](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][CH:16]=[CH:15]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.C1COCC1.[Pd]>[C:1]1([S:7]([CH2:10][CH2:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][CH:16]=[CH:15]3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 15521560(E)-5-(2-(phenylsulfonyl)vinyl)-1H-indole

Product 1

HCID 461956503-Dealkyl eletriptanYield 85%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of (E)-5-(2-(phenylsulfonyl)vinyl)-1H-indole (5.0 g) in 50 ml methanol, 10 ml THF and 10% Pd/C (1.0 g) was subject to hydrogenation at 45-50 psi. Upon completion of the reaction the catalyst was filtered off and the solvent removed under vacuum to provide the title compound in about 85-90% yield as an off-white solid. 1H NMR CDCl3 δ=8.15 (bs, NH), 7.93-8.00 (m, 2H), 7.53-7.70 (m, 3H), 7.38 (s, 1H), 7.30 (d, 1H), 7.20 (dd, 1H), 6.93 (dd, 1H), 6.42-6.48 (m, 1H), 3.37-3.46 (m, 2H), 2.99-3.17 (m, 2H). ESI Mass (M+23) 308.4

Workup

  1. customUpon completion of the reaction the catalyst
  2. filtrationwas filtered off
  3. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-af64ec8d04b24b10b8b5051a26788b79
Source dataset
uspto-grants-2014_01
Patent number
US08633239B2

Reaction notes

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