HCID 67227732, compound → HCID 53250744, compound

HRID 1515650Notes

Reaction equation

HRID 1515650 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:18]2[NH:28][C:21]3=[N:22][CH:23]=[C:24]([O:26][CH3:27])[CH:25]=[C:20]3[CH:19]=2)=[CH:12][CH:13]2[CH2:17][CH2:16][CH2:15][O:14]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>[Pd].CO>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:18]2[NH:28][C:21]3=[N:22][CH:23]=[C:24]([O:26][CH3:27])[CH:25]=[C:20]3[CH:19]=2)[CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][O:14]2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 67227732HCID 67227732, compound

Product 1

HCID 53250744HCID 53250744, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-furan-2-yl)-vinyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine (315 mg, 0.79 mmol) and 10% palladium on activated carbon (100 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-furan-2-yl)-ethyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine (60 mg, 18.9%) as a light yellow solid: LC/MS m/e calcd for C21H24N2O4S [M+H]+ 401.5, observed 401.3.

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-937bd796769f42f5ac04dc5ee9f3f489
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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