2-{2-cyclopentyl-1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-vinyl}-1H-pyrrolo[2,3-b]pyridine → 2-{2-cyclopentyl-1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridine

HRID 1515816Notes

Reaction equation

HRID 1515816 reaction equation
[CH:1]1([CH:6]=[C:7]([C:22]2[NH:30][C:25]3=[N:26][CH:27]=[CH:28][CH:29]=[C:24]3[CH:23]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH2:18][O:19][CH2:20][CH3:21])(=[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:22]2[NH:30][C:25]3=[N:26][CH:27]=[CH:28][CH:29]=[C:24]3[CH:23]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH2:18][O:19][CH2:20][CH3:21])(=[O:15])=[O:16])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 672291462-{2-cyclopentyl-1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-vinyl}-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 532521822-{2-cyclopentyl-1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridineYield 75.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-{2-cyclopentyl-1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-vinyl}-1H-pyrrolo[2,3-b]pyridine (900 mg, 2.12 mmol) and 10% palladium on activated carbon (270 mg) in methanol (300 mL) was heated at 50° C. under hydrogen (50 psi) for 16 h. The mixture was cooled to 25° C., the solids filtered off, washed with ethyl acetate and concentrated in vacuo. Purification 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) afforded 2-{2-cyclopentyl-1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridine (680 mg, 75%): LC/MS m/e calcd for C24H30N2O3S [M+H]+ 427.58, observed 427.4; 1H NMR (400 MHz, CD3OD) δ ppm 8.08-8.15 (m, 1H), 7.86-7.94 (m, 3H), 7.62 (d, J=8.3 Hz, 2H), 7.07 (dd, J=7.7, 4.9 Hz, 1H), 6.41 (s, 1H), 4.34 (t, J=7.8 Hz, 1H), 3.75 (t, J=5.8 Hz, 2H), 3.48 (t, J=5.7 Hz, 2H), 3.28 (q, J=7.0 Hz, 2H), 2.26-2.35 (m, 1H), 2.07-2.20 (m, 1H), 1.62-1.89 (m, 5H), 1.46-1.57 (m, 2H), 1.19-1.33 (m, 2H), 0.86 (t, J=6.9 Hz, 3H).

Workup

  1. temperatureThe mixture was cooled to 25° C.
  2. filtrationthe solids filtered off
  3. washwashed with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-b390bc79a4d4466fa6bd764b4cf322ba
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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