Pyridine → 1234321-81-3

HRID 2061008Notes

Reaction equation

HRID 2061008 reaction equation
[CH3:1][O:2][C:3](=[O:17])/[CH:4]=[C:5](\[NH2:16])/[CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=1[F:15].N1C=CC=CC=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>C1COCC1>[CH3:25][C:24]([NH:16]/[C:5](/[CH2:6][C:7]1[C:8]([F:15])=[CH:9][C:10]([F:14])=[C:11]([F:13])[CH:12]=1)=[CH:4]\[C:3]([O:2][CH3:1])=[O:17])=[O:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 49817597HCID 49817597, compound

Product 1

HCID 468365781234321-81-3Yield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (Z)-methyl-3-amino-4-(2,4,5-trifluorophenyl)but-2-enoate (4.90 g, 20 mmol) of Example 2, pyridine (4.8 ml) and acetic anhydride (4.80 g, mmol) in THF (30 ml) was heated to reflux for 16 h. The reaction mixture was stirred at room temperature, quenched with 1N HCl, and extracted with ethyl acetate (3×20 ml). The combined organic phase was washed with saturated sodium bicarbonate, then brine, then dried over sodium sulfate. Concentration was followed by purification by flash chromatography to afford 4.03 g of product (70.3%). 1H NMR (300 MHz, CDCl3) 11.14 (s, 1H) 7.10-7.00 (m, 1H), 6.96-6.87 (m, 1H), 4.81 (s, 1H), 4.14 (s, 2H), 3.70 (s, 3H), 2.14 (s, 3H).

Workup

  1. temperatureto reflux for 16 h
  2. customquenched with 1N HCl
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. washThe combined organic phase was washed with saturated sodium bicarbonate
  5. dry with materialbrine, then dried over sodium sulfate
  6. concentrationConcentration
  7. customwas followed by purification by flash chromatography

Sources & evidence

ORD record
ord-f7ac05a4aa3d4b55b87c220f34f150d0
Source dataset
uspto-grants-2012_10
Patent number
US08278486B2

Reaction notes

Loading…