HCID 86618291, compound → HCID 86618292, compound

HRID 2264609Notes

Reaction equation

HRID 2264609 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:27]=[C:26]([N:28]=[N+]=[N-])[N:25]=[CH:24][N:23]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1>C1COCC1.[Pd]>[F:31][C:2]([F:1])([F:32])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:27]=[C:26]([NH2:28])[N:25]=[CH:24][N:23]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 86618291HCID 86618291, compound

Product 1

HCID 86618292HCID 86618292, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4.58 g (10.4 mMol) 5-(6-azido-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide in 150 ml THF are hydrogenated in the presence of 0.8 g Pd/C (10%; Engelhard 4505). The catalyst is filtered off and the filtrate concentrated. The residue is dissolved in EtOAc and H2O and the aqueous layer extracted twice with EtOAc. The organic layers are washed with brine, dried (Na2SO4) and concentrated, yielding the title compound: m.p.: 186-187° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate concentrated
  3. dissolutionThe residue is dissolved in EtOAc
  4. extractionH2O and the aqueous layer extracted twice with EtOAc
  5. washThe organic layers are washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c46ddee402ac40e89db8adb5c3e8b851
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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