2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-b]pyridine → 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-b]pyridine

HRID 1515637Notes

Reaction equation

HRID 1515637 reaction equation
[CH:1]1([CH:6]=[C:7]([C:18]2[NH:31][C:21]3=[N:22][CH:23]=[C:24]([O:26][CH2:27][CH2:28][O:29][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:31][C:21]3=[N:22][CH:23]=[C:24]([O:26][CH2:27][CH2:28][O:29][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

Participants

4

Reactant 1

HCID 672277622-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 532505852-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-b]pyridineYield 38.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-b]pyridine (260 mg, 0.59 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-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-b]pyridine (100 mg, 38.5%) as a white solid: LC/MS m/e calcd for C24H30N2O4S [M+H]+ 443.58, observed 443.3; 1H NMR (400 MHz, CDCl3) δ ppm 10.76 (br. s., 1H), 7.96 (br. s., 1H), 7.86-7.93 (m, 2H), 7.72 (s, 1H), 7.50-7.60 (m, 2H), 6.40 (br. s., 1H), 4.30 (t, J=7.6 Hz, 1H), 4.22 (br. s., 2H), 3.80 (br. s., 2H), 3.48 (s, 3H), 3.02-3.08 (m, 3H), 2.09-2.29 (m, 2H), 1.59-1.85 (m, 5H), 1.44-1.56 (m, 2H), 1.13-1.28 (m, 2H).

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-73a8e64dad124a31aa213783476e6430
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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