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

HRID 1515925Notes

Reaction equation

HRID 1515925 reaction equation
[CH:1]1([CH:6]=[C:7]([C:18]2[NH:27][C:21]3=[N:22][CH:23]=[C:24]([CH3:26])[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:27][C:21]3=[N:22][CH:23]=[C:24]([CH3:26])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:15])=[O:16])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 672292692-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 583052462-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-methyl-1H-pyrrolo[2,3-b]pyridineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-methyl-1H-pyrrolo[2,3-b]pyridine (240 mg, 0.63 mmol) and 10% palladium on activated carbon (100 mg) in methanol (50 mL) was heated at 50° C. under hydrogen (50 psi) for 5 h. After cooling to room temperature, the catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo. The residue was 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-methyl-1H-pyrrolo[2,3-b]pyridine as a white solid (150 mg, 100%): LC/MS m/e calcd for C22H26N2O2S [M+H]+ 383.53, observed 382.9; 1H NMR (400 MHz, CD3OD) δ ppm 8.21 (s, 1H), 8.06 (s, 1H), 7.87-7.91 (m, J=8.1 Hz, 2H), 7.56-7.61 (m, J=8.3 Hz, 2H), 6.61 (s, 1H), 4.34 (t, J=7.8 Hz, 1H), 2.99-3.10 (m, 3H), 2.48 (s, 3H), 2.22-2.30 (m, 1H), 2.10-2.18 (m, 1H), 1.58-1.86 (m, 5H), 1.43-1.54 (m, 2H), 1.16-1.30 (m, 2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe catalyst was removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified

Sources & evidence

ORD record
ord-0bc9a65e9027440391ee92ea51708d46
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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