Triethylamine → HCID 178418902, compound

HRID 7805

Reaction equation

HRID 7805 reaction equation
[NH2:1][C:2]1[C:3]([OH:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C(N(CC)CC)C.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C.CO>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:19]([C:18]([F:17])([F:28])[F:29])=[CH:20][CH:21]=2)[C:3]([OH:9])=[N:4][CH:5]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 178418959HCID 178418959, compound

Product 1

HCID 178418902HCID 178418902, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-amino-5-bromopyridin-2-ol from Step C (1.5 g, 7.9 mol) and triethylamine (1.64 mL, 11.9 mol) in tetrahydrofuran (15.8 mL) at 0 C was added dropwise 4-trifluoromethylbenzoyl chloride (1.2 mL, 7.9 mol). The reaction mixture was stirred at 0° C. for 1 h and warmed to room temperature for 15 h. Potassium carbonate (1.64 g, 11.9 mol) and methanol (15.8 mL) were added and the reaction mixture was stirred at room temperature for 6 h. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with saturated ammonium chloride solution and brine. The separated organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. Purification by medium pressure liquid chromatography on silica gel (1:5 ethyl acetate/hexanes) gave 1.72 g (60%) of the title compound.

Workup

  1. temperaturewarmed to room temperature for 15 h
  2. stirringthe reaction mixture was stirred at room temperature for 6 h
  3. washwashed with saturated ammonium chloride solution and brine
  4. dry with materialThe separated organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by medium pressure liquid chromatography on silica gel (1:5 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-398716f2fe394a7f9a626f6e1dd67830
Source dataset
uspto-grants-2006_08
Patent number
US07087622B2

Linked notes

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