Triethylamine → HCID 57860705, compound

HRID 1947157Notes

Reaction equation

HRID 1947157 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-bfd4e8cbc26542cdbfec8d8d1c6f4655
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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