Dimethylformamide → HCID 21088594, compound

HRID 350741Notes

Reaction equation

HRID 350741 reaction equation
Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][C:16]([O:18]C)=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[N:21]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[N:6]=[C:2]([N:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[N:21]3)[O:3][C:4]=2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 92211H-IndazoleHCID 11430Potassium CarbonateHCID 10990225Methyl 3-[2-chloro-4-(4-chlorophenyl)-5-oxazolyl]propionate

Product 1

HCID 21088594HCID 21088594, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 3-[2-chloro-4-(4-chlorophenyl)-5-oxazolyl]propionate (1.50 g), 1H-indazole (1.18 g), potassium carbonate (1.38 g) and N,N-dimethylformamide (20 mL) was stirred at 120° C. for 3 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The obtained crystals were collected by filtration, dried and dissolved in a mixed solvent of tetrahydrofuran (20 mL) and ethanol (20 mL). A 1N aqueous sodium hydroxide solution (10 mL) was added, and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was acidified with 1N aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The obtained crystals were collected by filtration using isopropyl ether and dried to give 3-[4-(4-chlorophenyl)-2-(1H-indazol-1-yl)-5-oxazolyl]propionic acid (824 mg, yield 45%) as pale-yellow prism crystal. melting point: 204–205° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. filtrationThe obtained crystals were collected by filtration
  6. customdried
  7. dissolutiondissolved in a mixed solvent of tetrahydrofuran (20 mL) and ethanol (20 mL)
  8. additionA 1N aqueous sodium hydroxide solution (10 mL) was added
  9. stirringthe mixture was stirred at room temperature for 2 hrs
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe organic layer was washed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated
  14. filtrationThe obtained crystals were collected by filtration
  15. customdried

Sources & evidence

ORD record
ord-ae1800157a9642d7849c47dbe200b8ab
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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