HCID 59596360, compound → HCID 59596396, compound

HRID 2264599Notes

Reaction equation

HRID 2264599 reaction equation
[F:1][C:2]([F:31])([F:30])[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](Cl)[N:25]=[C:24]([NH2:29])[N:23]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1>CCO.CCOC(C)=O.[Pd]>[F:30][C:2]([F:1])([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]=[CH:26][N:25]=[C:24]([NH2:29])[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 59596360HCID 59596360, compound

Product 1

HCID 59596396HCID 59596396, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of 170 mg (0.38 mMol) 5-(2-amino-6-chloro-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide in 19 ml EtOH/EtOAc 1:1 in hydrogenated in the presence of 80 mg Pd/C (10%; Engelhard 4505). The catalyst is filtered off and the filtrate diluted with EtOAc and sat. Na2CO3/H2O 1:1. The aqueous layer is extracted twice with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; EtOAc/hexane 3:2→EtOAc) gives the title compound: MS: [M+1]+=416; TLC(hexane/EtOAc 3:7): Rf=0.14; HPLC: AtRet=12.0.

Workup

  1. filtrationThe catalyst is filtered off
  2. additionthe filtrate diluted with EtOAc and sat. Na2CO3/H2O 1:1
  3. extractionThe aqueous layer is extracted twice with EtOAc
  4. washThe organic phases are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-53a65808f900492ab85078c760a15300
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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