(2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethyl)-dimethyl-amine → (2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethyl)-dimethyl-amine

HRID 1515640Notes

Reaction equation

HRID 1515640 reaction equation
[CH:1]1([CH:6]=[C:7]([C:18]2[NH:32][C:21]3=[N:22][CH:23]=[C:24]([O:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:32][C:21]3=[N:22][CH:23]=[C:24]([O:26][CH2:27][CH2:28][N:29]([CH3:30])[CH3:31])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 67227945(2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethyl)-dimethyl-amine

Product 1

HCID 53250587(2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethyl)-dimethyl-amineYield 10%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethyl)-dimethyl-amine (200 mg, 0.44 mmol) and 10% palladium on activated carbon (40 mg) in methanol (200 mL) was heated at 50° C. under hydrogen (50 psi) for 6 h. The mixture was cooled to room temperature. The catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo and purified using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) to afford (2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethyl)-dimethyl-amine (20 mg, 10%) as a white solid: LC/MS m/e calcd for C25H33N3O3S [M+H]+ 456.62, observed 456.3; 1H NMR (400 MHz, CD3OD) δ ppm 1.26 (m, 2 H), 1.51 (m, 2H), 1.58-1.90 (m, 5H, H), 2.11 (m, 1H), 2.27 (m, 1H), 2.44 (s, 6H), 2.89 (t, J=5.4 Hz, 2H), 3.10 (s, 3H), 4.19 (t, J=5.4 Hz, 2H), 4.30 (t, J=8.0 Hz, 1H), 6.35 (s, 1H), 7.55 (d, J=2.8 Hz, 1H), 7.61 (d, J=8.3 Hz, 2H), 7.9 (m, 3H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe catalyst was removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified

Sources & evidence

ORD record
ord-43bfa220769441e98a22a5a3381a619e
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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