Hydrochloric Acid → HCID 19086721, compound

HRID 1464573Notes

Reaction equation

HRID 1464573 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([F:22])[C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][NH:11]2)=[CH:7][CH:6]=1.[H-].[Na+].Br[CH:26]([CH3:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28].Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[C:14]([F:22])[C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH:26]([CH3:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:7][CH:6]=1.[Cl:1][C:2]1[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[C:14]([F:22])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:12]([CH:13]=1)=[N:11][N:10]([CH:26]([CH3:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:9]=2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionateHCID 19086712HCID 19086712, compound

Product 2

HCID 19086721HCID 19086721, compoundHCID 19086731HCID 19086731, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

6-(2-Chloro-6-fluoro-4-trifluoromethylphenoxy)indazole (0.7 g) was dissolved in dry DMF (1.5 cm3) and cooled in a waterbath when 50% sodium hydride (0.1 g) was added portionwise with stirring. The mixture was stirred for 10 minutes and ethyl 2-bromopropionate (0.42 g) was added. The mixture was stirred with water cooling for 5 minutes and then at room temperature for 8.5 hours. The reaction was poured into water (15cm3) containing 2M hydrochloric acid (1 cm3) and the mixture extracted with ethyl acetate three times. The organic phase was combined, washed with water, dried (MgSO4), filtered, and the solvent removed from the filtrate under vacuum. The residue was purified by flash chromatography (hexane: TBME, 7:3) to give compound 1, ethyl 2-[6-(2-chloro-6-fluoro-4-trifluoromehylphenoxy)indazol-1-yl]propionate (0.51 g) as a colorless oil and compound 33 ethyl 2-[6-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)indazol-2-yl]propionate (0.154 g) as an oil.

Workup

  1. additionwas added portionwise
  2. stirringThe mixture was stirred for 10 minutes
  3. extractionthe mixture extracted with ethyl acetate three times
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed from the filtrate under vacuum
  8. customThe residue was purified by flash chromatography (hexane: TBME, 7:3)

Sources & evidence

ORD record
ord-b803d9e33e14449fa641579bf9e72baf
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

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