Triethylamine → 6-(Pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid ethyl ester

HRID 556351Notes

Reaction equation

HRID 556351 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18](Cl)[N:17]=3)=[CH:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:2].CCN(CC)CC>CN(C=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][N:17]=3)=[CH:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 866266246-(2-Chloro-pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid ethyl ester

Product 1

HCID 669929496-(Pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

300 mg (0.938 mMol) 6-(2-chloro-pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid ethyl ester in 3 ml DMF and 262 μl (1.88 mMol) Et3N are hydrogenated in presence of 120 mg Pd/C (10%; Engelhard 4505). The catalyst is filtered off, the filtrate concentrated, the residue re-dissolved in EtOAc and water, the aq. layer separated off and extracted with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/EtOAc 9:1→4:1) gives the title compound: MS: [M+1]+=286; TLC(hexane/EtOAc 1:1): Rf=0.30.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate concentrated
  3. dissolutionthe residue re-dissolved in EtOAc
  4. customwater, the aq. layer separated off
  5. extractionextracted with EtOAc
  6. washThe organic layers are washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-83f8df568c5a418f901e7844a0bb0d18
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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