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

HRID 1515659Notes

Reaction equation

HRID 1515659 reaction equation
[CH:1]1([CH:6]=[C:7]([C:18]2[NH:30][C:21]3=[N:22][CH:23]=[C:24]([O:26][CH2:27][CH2:28][OH:29])[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:30][C:21]3=[N:22][CH:23]=[C:24]([O:26][CH2:27][CH2:28][OH:29])[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 672286052-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethanol

Product 1

HCID 532509172-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethanolYield 55.1%

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}-ethanol (460 mg, 1.08 mmol) and 10% palladium on activated carbon (100 mg) in methanol (200 mL) was heated at 50° C. under hydrogen (50 psi) for 6 h. The mixture was cooled to room temperature before the catalyst was removed by filtration. 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}-ethanol (236 mg, 55.1%) as a white solid: LC/MS m/e calcd for C23H28N2O4S [M+H]+ 429.55, observed 429.5; 1H NMR (400 MHz, CD3OD) δ ppm 7.98 (br. s., 1H), 7.90 (d, J=8.3 Hz, 3H), 7.60 (d, J=8.1 Hz, 2H), 6.53 (s, 1H), 4.33 (t, J=7.8 Hz, 1H), 4.16 (t, J=4.5 Hz, 2H), 3.90 (t, J=4.5 Hz, 2H), 3.09 (s, 3H), 2.23-2.31 (m, 1H), 2.09-2.18 (m, 1H), 1.60-1.87 (m, 5H), 1.44-1.56 (m, 2H), 1.17-1.30 (m, 2H).

Workup

  1. temperatureThe mixture was cooled to room temperature before the catalyst
  2. customwas removed by filtration
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified

Sources & evidence

ORD record
ord-29b9f3e5a75e40b3b95de4335dbbc7f3
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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