Water → HCID 68153160, compound

HRID 1805267Notes

Reaction equation

HRID 1805267 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([C:18]2[CH:19]=[N:20][N:21]([CH2:27][CH2:28][O:29]C)[C:22]=2[C:23]([F:26])([F:25])[F:24])[O:11][N:10]=1.O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([C:18]2[CH:19]=[N:20][N:21]([CH2:27][CH2:28][OH:29])[C:22]=2[C:23]([F:25])([F:24])[F:26])[O:11][N:10]=1

Participants

4

Reactant 2

HCID 962WaterHCID 68153301HCID 68153301, compound

Product 1

HCID 68153160HCID 68153160, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(2-methoxyethyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate (example I-102) (27 mg, 0.06 mmol) in CH2Cl2 (1 mL) was added Bortribromide (0.06 mmol). The mixture was stirred at 0° C. for 1 h. The mixture was poured into iced water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting oil was purified by pTLC (PE:EE 1:1) to yield example I-83 as an oil (10 mg, 34%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting oil was purified by pTLC (PE:EE 1:1)
  6. customto yield example

Sources & evidence

ORD record
ord-fcb3cc57b4574b25aece2b95ed0bead9
Source dataset
uspto-grants-2013_01
Patent number
US08354436B2

Reaction notes

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