HCID 178454104, compound → HCID 178419706, compound

HRID 707414Notes

Reaction equation

HRID 707414 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:11][C@H:10]([N:12]2[C:16]3=[N:17][CH:18]=[C:19]([Br:21])[CH:20]=[C:15]3[C:14]([F:23])([F:22])[C:13]2=[O:24])[CH2:9]1)(C)(C)C>CCO.[Pd]>[BrH:21].[NH2:7][C@H:8]1[CH2:11][C@H:10]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[C:14]([F:23])([F:22])[C:13]2=[O:24])[CH2:9]1

Participants

4

Reactant 1

HCID 178454104HCID 178454104, compound

Product 1

HCID 178419706HCID 178419706, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium (10 weight percent on activated carbon, 0.0607 g, 0.057 mmol) was added to a mixture of tert-butyl(trans-3-(5-bromo-3,3-difluoro-2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutyl)carbamate (0.477 g, 1.141 mmol) in EtOH (5 mL) under an argon atmosphere. The reaction mixture was placed under a hydrogen atmosphere (balloon) and stirred at room temperature for 7 h. The reaction mixture was filtered through CELITE®, and the filtrate was concentrated. The resulting white solid was triturated with DCM and filtered to yield the title compound (0.084 g, 0.262 mmol, 23.0% yield) as a white solid. M+1: 240.1.

Workup

  1. filtrationThe reaction mixture was filtered through CELITE®
  2. concentrationthe filtrate was concentrated
  3. customThe resulting white solid was triturated with DCM
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c1f93e11398a4cd38acc00f3dfac0e0c
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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