HCID 67228192, compound → HCID 58305248, compound

HRID 1515663Notes

Reaction equation

HRID 1515663 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:19]2[NH:29][C:22]3=[N:23][CH:24]=[C:25]([O:27][CH3:28])[CH:26]=[C:21]3[CH:20]=2)=[CH:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>[Pd].CO>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([C:19]2[NH:29][C:22]3=[N:23][CH:24]=[C:25]([O:27][CH3:28])[CH:26]=[C:21]3[CH:20]=2)[CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 67228192HCID 67228192, compound

Product 1

HCID 58305248HCID 58305248, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-pyran-4-yl)-vinyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine (180 mg, 0.44 mmol) and 10% palladium on activated carbon (50 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-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-pyran-4-yl)-ethyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine (80 mg, 44.4%) as a white solid: LC/MS m/e calcd for C22H26N2O4S [M+H]+ 415.53, observed 415.2; 1H NMR (400 MHz, CD3OD) δ ppm 7.84-7.92 (m, 3H), 7.61 (d, J=8.3 Hz, 2H), 7.50 (d, J=2.5 Hz, 1H), 6.34 (s, 1H), 4.42 (t, J=8.0 Hz, 1H), 3.84-3.93 (m, 5H), 3.32-3.26 (m, 2H), 3.09 (s, 3H), 2.18-2.27 (m, 1H), 1.97-2.05 (m, 1H), 1.69-1.76 (m, 2H), 1.50 (ddt, J=10.8, 7.1, 3.5 Hz, 1H), 1.31-1.42 (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-dd5855e4e0d34e86a212200874e68794
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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