HCID 67229384, compound → HCID 67228593, compound

HRID 1515877Notes

Reaction equation

HRID 1515877 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([C:17]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=3)=[CH:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[NH:14][C:11]2=[N:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([CH:17]([C:25]3[CH:26]=[CH:27][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][CH:30]=3)[CH2:18][CH:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[NH:14][C:11]2=[N:12][CH:13]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 67229384HCID 67229384, compound

Product 1

HCID 67228593HCID 67228593, compoundYield 100%

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]pyridin-5-yl}-carbamic acid tert-butyl ester (520 mg, 1.05 mmol) and 10% palladium on activated carbon (0.2 g) in methanol (150 mL) was heated at 50° C. under hydrogen (5 atm) 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 {2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-pyran-4-yl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-carbamic acid tert-butyl ester (520 mg, 100%) which was used in the next step without purification: LC/MS m/e calcd for C26H33N3O5S [M+H]+ 500.63, observed 500.2.

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

Sources & evidence

ORD record
ord-2abe8ba3d8a44ee186a2a84b98688e2f
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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