2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(3-methoxy-prop-1-ynyl)-1H-pyrrolo[2,3-b]pyridine → HCID 53251247, compound

HRID 1515695Notes

Reaction equation

HRID 1515695 reaction equation
[CH:1]1([CH:6]=[C:7]([C:18]2[NH:31][C:21]3=[N:22][CH:23]=[C:24]([C:26]#[C: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]([CH2:26][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 672289752-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(3-methoxy-prop-1-ynyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 53251247HCID 53251247, compoundYield 32.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(3-methoxy-prop-1-ynyl)-1H-pyrrolo[2,3-b]pyridine (302 mg, 0.7 mmol) and 10% palladium on activated carbon (80 mg) in methanol (250 mL) was heated at 50° C. under hydrogen (50 psi) for 8 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. 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-methanesulfonyl-phenyl)-ethyl]-5-(3-methoxy-propyl)-1H-pyrrolo[2,3-b]pyridine (100 mg, 32.5%) as a colorless oil: LC/MS m/e calcd for C25H32N2O3S [M+H]+ 441.61, observed 441.1; 1H NMR (400 MHz, CD3OD) δ ppm 8.25 (s, 1H), 8.10 (br. s., 1H), 7.90-7.95 (m, J=8.1 Hz, 2H), 7.60-7.65 (m, J=8.3 Hz, 2H), 6.65 (s, 1H), 4.39 (t, J=7.8 Hz, 1H), 3.43 (t, J=6.2 Hz, 2H), 3.35 (s, 3H), 3.11 (s, 3H), 2.88 (t, J=7.6 Hz, 2H), 2.26-2.34 (m, 1H), 2.13-2.22 (m, 1H), 1.92-1.99 (m, 2H), 1.63-1.89 (m, 5H), 1.46-1.58 (m, 2H), 1.19-1.34 (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. customPurification

Sources & evidence

ORD record
ord-9302b736221e473ca9a02f2cd7dc707f
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

Loading…