Water → HCID 67058147, compound

HRID 1515088Notes

Reaction equation

HRID 1515088 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:17][CH2:18][CH3:19])[CH2:9][CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])=[CH:4][N:3]=1.[F:20][C:21]([F:31])([F:30])[C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1.CC(C)([O-])C.[K+].O>COCCOC.C(C1C=CC=C(C(C)C)C=1N1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C1=[Pd-]C1C(Cl)=CC=CN=1)(C)C>[CH2:18]([O:17][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:27][CH2:26][C:25]2[CH:24]=[CH:23][C:22]([C:21]([F:20])([F:30])[F:31])=[CH:29][CH:28]=2)=[N:3][CH:4]=1)[CH2:9][CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 768044-(Trifluoromethyl)benzylamineHCID 23665647Potassium tert-butoxideHCID 86651745HCID 86651745, compound

Product 1

HCID 67058147HCID 67058147, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 178439030HCID 178439030, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-5-(1,3,3-triethoxypropyl)pyridine (328 mg, 0.987 mmol) produced in Example 17 (17B) and 4-trifluoromethylbenzylamine (346 mg, 1.98 mmol) were dissolved in 1,2-dimethoxyethane (10 mL), and potassium tert-butoxide (346 mg, 1.98 mmol) and [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) (34 mg, 5 mol %) were added thereto, and then, the resulting mixture was stirred under a nitrogen atmosphere at 100° C. for 3 hours. After the reaction solution was cooled to room temperature, water was added thereto, and the organic matter was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 50:50 (v/v)), whereby the objective title compound was obtained as a colorless oily substance (25 mg, yield: 6%).

Workup

  1. temperatureAfter the reaction solution was cooled to room temperature
  2. extractionthe organic matter was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
  7. customwas obtained
  8. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 50:50 (v/v)), whereby the objective title compound
  9. customwas obtained as a colorless oily substance (25 mg, yield: 6%)

Sources & evidence

ORD record
ord-d5162fd27ad54ffdbb22e89324a82bb0
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

Loading…