HCID 67228577, compound → HCID 58305247, compound

HRID 1515873Notes

Reaction equation

HRID 1515873 reaction equation
[CH:1]1([CH:6]=[C:7]([C:18]2[NH:28][C:21]3=[N:22][C:23]([O:26][CH3:27])=[CH:24][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:28][C:21]3=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][CH:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 67228577HCID 67228577, compound

Product 1

HCID 58305247HCID 58305247, compoundYield 8.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-6-methoxy-1H-pyrrolo[2,3-b]pyridine (0.22 g, 0.56 mmol) and 10% palladium on activated carbon (0.2 g) in methanol (150 mL) was heated at 50° C. under hydrogen (50 psi) for 12 h. After cooling to room temperature, the catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo to give a residue which 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]-6-methoxy-1H-pyrrolo[2,3-b]pyridine (18 mg, 8.2%) as a white solid: LC/MS m/e calcd for C22H26N2O3S [M+H]+ 399.53, observed 399.3; 1H NMR (400 MHz, CDCl3) δ ppm 1.16 (m, 2H), 1.48 (m, 2H), 1.56-1.85 (m, 5H, H), 2.04 (m, 1H), 2.17 (m, 1H), 3.05 (s, 3H), 3.90 (s, 3H), 4.14 (t, J=7.7 Hz, 1H), 6.29 (s, 1H), 6.55 (d, J=8.5 Hz, 1H), 7.42 (d, J=8.1 Hz, 2H), 7.73 (d, J=8.5 Hz, 1H), 7.86 (d, J=8.1 Hz, 2H), 8.31 (s, 1H).

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. customto give a residue which
  6. customwas purified

Sources & evidence

ORD record
ord-5726d4bd1ad449379479b44ddc8a3db8
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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