HCID 67228668, compound → HCID 53302845, compound

HRID 1515761Notes

Reaction equation

HRID 1515761 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:19]2[NH:27][C:22]3=[N:23][CH:24]=[CH:25][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:27][C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)[CH2:12][CH:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 67228668HCID 67228668, compound

Product 1

HCID 53302845HCID 53302845, compoundYield 27%

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]-1H-pyrrolo[2,3-b]pyridine (260 mg, 6.8 mmol) and 10% palladium on activated carbon (66 mg) in methanol (200 mL) was heated at 50° C. under hydrogen (50 psi) and kept for 16 h. The mixture was cooled to 25° C., the catalyst 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-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-pyran-4-yl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (60 mg, 27%) as a white solid: LC/MS m/e calcd for C21H24N2O3S [M+H]+ 385.50, observed 385.1.

Workup

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

Sources & evidence

ORD record
ord-d7555e55c213458e8ed6eac93f80fc37
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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