Acetic Acid → HCID 21865164, compound

HRID 857621Notes

Reaction equation

HRID 857621 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9]2[C:4](=[CH:5][C:6]([O:16][C:17]3[CH:22]=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)[N:20]=[CH:19][N:18]=3)=[CH:7][CH:8]=2)[N:3]=1.CC(O)=O.O.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.[Zn]>[F:15][C:12]([F:13])([F:14])[C:10]1[C:9]2[C:4](=[CH:5][C:6]([O:16][C:17]3[CH:22]=[C:21]([C:23]4[CH:24]=[CH:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=4)[N:20]=[CH:19][N:18]=3)=[CH:7][CH:8]=2)[N:3]=[CH:2][CH:11]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 21865065HCID 21865065, compound

Product 1

HCID 21865164HCID 21865164, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a 100-mL, round-bottomed flask containing a solution of 2-chloro-4-trifluoromethyl-7-[6-(4-trifluromethyl-phenyl)-pyrimidin-4-yloxy]-quinoline, (Example 22(b)), (0.25 g, 0.53 mmol) in EtOAc (20 mL) was added Zn (0.87 g, 13 mmol, Aldrich), AcOH (61 mg, 1.1 mmol), and water (40 mg, 1.1 mmol). The mixture was heated at 70° C. with stirring for 2.5 h. After cooling to room temperature, 5% aq. Na2CO3 was added and the reaction mixture was extracted with EtOAc (30 mL). The organic phase was washed with water (2×10 mL), dried over Na2SO4, filtered, and concentrated in vacuum. Purification of the residue by silica gel chromatography (gradient: 3:1 hexanes:EtOAc) gave the title compound. Mp: 129–131° C. MS (ESI, pos. ion) m/z: 436 (M+1).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe reaction mixture was extracted with EtOAc (30 mL)
  3. washThe organic phase was washed with water (2×10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customPurification of the residue by silica gel chromatography (gradient: 3:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-af256dd78ab4433e8f7612820c510bc4
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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