Triethylamine → HCID 57860705, compound

HRID 1513610Notes

Reaction equation

HRID 1513610 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:28].C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.Br[C:50]1[CH:55]=[CH:54][N:53]=[C:52]([C:56]([F:59])([F:58])[F:57])[CH:51]=1>CN(C=O)C.O>[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:31][CH2:32][N:33]([C:50]2[CH:55]=[CH:54][N:53]=[C:52]([C:56]([F:59])([F:58])[F:57])[CH:51]=2)[CH2:34][CH2:35]1)=[O:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 234369504-Bromo-2-(trifluoromethyl)pyridineHCID 57860479HCID 57860479, compound

Product 1

HCID 57860705HCID 57860705, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of the compound of Example 77 (300 mg, 0.59 mmol), potassium carbonate (204 mg, 1.5 mmol) and triethylamine (0.082 mL, 0.59 mmol) in DMF (3.0 mL) was heated to 80° C., 4-bromo-2-(trifluoromethyl)pyridine (133 mg, 0.59 mmol) was added, and the mixture was stirred at 100° C. for 23 hr. The reaction mixture was diluted with water, and extracted 3 times with ethyl acetate. The extract was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=50/50-100/0) and recrystallized from ethyl acetate-hexane to give the title compound (126 mg, 35%) as a white solid.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=50/50-100/0)
  5. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-efcd80fab9a44085bcebf4e577a99278
Source dataset
uspto-grants-2012_07
Patent number
US08217176B2

Reaction notes

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