Potassium Hydroxide → HCID 59529753, compound

HRID 1952368Notes

Reaction equation

HRID 1952368 reaction equation
Cl[CH:2]1[C:7]([O:8][C:9]2[CH:14]=[C:13]([Br:15])[CH:12]=[C:11]([Br:16])[CH:10]=2)=[C:6]([C:17]([F:20])([F:19])[F:18])[CH:5]=[CH:4][NH:3]1.[OH-:21].[K+]>C(O)(C)(C)C>[Br:16][C:11]1[CH:10]=[C:9]([CH:14]=[C:13]([Br:15])[CH:12]=1)[O:8][C:7]1[C:2](=[O:21])[NH:3][CH:4]=[CH:5][C:6]=1[C:17]([F:20])([F:19])[F:18]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86646329HCID 86646329, compound

Product 1

HCID 59529753HCID 59529753, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2-chloro-3-(3,5-dibromophenoxy)-4-(trifluoromethyl)-1,2-dihydropyridine (1.64 g, 3.80 mmol) and potassium hydroxide (0.640 g, 11.4 mmol) were dissolved in tert-butanol in a round bottom flask and placed in an oil bath at 75° C. under N2. After 16 hours, the reaction mixture was allowed to cool to room temperature and quenched with saturated aqueous ammonium chloride (25 mL). This mixture was diluted with water (25 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (2×50 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure to give the title compound as a white solid. 1H NMR (DMSO-d6) δ 12.68 (s, 1H), 7.58 (d, J=6.8 Hz, 1H), 7.54-7.52 (m, 1H), 7.24-7.22 (m, 2H), 6.47 (d, J=Hz, 1H). LRMS (M+1)=413.5.

Workup

  1. customplaced in an oil bath at 75° C. under N2
  2. customquenched with saturated aqueous ammonium chloride (25 mL)
  3. additionThis mixture was diluted with water (25 mL)
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. washThe combined organic extracts were washed with brine (2×50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5e1f239da67b4f349083b085f69a4932
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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