Acetic Acid → HCID 68663763, compound

HRID 452679Notes

Reaction equation

HRID 452679 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:12][C:13]([F:23])([F:22])[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O.C(O)(=O)C.[Na]>O1CCCC1.C(OCC)(=O)C>[F:12][C:13]([F:22])([F:23])[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 679903-(Trifluoromethyl)benzaldehydeHCID 236984Methyl 2-aminopyridine-4-carboxylateHCID 5360545Sodium

Product 1

HCID 68663763HCID 68663763, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 2-aminoisonicotinate (1.52 g, 10.00 mmol), 3-(trifluoromethyl)benzaldehyde (2.09 g, 12.00 mmol) and acetic acid (0.572 mL, 10.00 mmol) in tetrahydrofuran (30 mL) was stirred at room temperature for 30 min. To this reaction mixture was added sodium triacetoxyhydroborate (4.46 g, 20.00 mmol), and the resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1-9/1) to give the title compound (1.06 g, yield 34%) as a colorless oil.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1-9/1)

Sources & evidence

ORD record
ord-da0442cefbd7440f9ccaf02fe3ac51ee
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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