4-Vinylpyridine → HCID 5327625, compound

HRID 724921Notes

Reaction equation

HRID 724921 reaction equation
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12](I)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2].[CH:21]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)=[CH2:22].C(N(CC)CC)C.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>CN(C)C=O.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12](/[CH:22]=[CH:21]/[C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2]

Participants

8

Reactant 4

HCID 75024-VinylpyridineHCID 8471TriethylamineHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 10547779HCID 10547779, compound

Product 1

HCID 5327625HCID 5327625, compoundYield 73.6%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture containing 5,11-dihydro-11-ethyl-8-iodo-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]-diazepin-6-one (0.7 g, 1.9 mmol), 4-vinylpyridine (0.3 mL, 2.9 mmol), bis(triphenylphosphine)palladium(II) chloride (60 mg, 0.09 mmol), triethylamine (1.8 mL, 12.8 mmol), and 1 crystal of 2,6-di-tert-butyl-4-methylphenol in 4 mL of N,N-dimethylformamide was heated at 125° C. under argon for 3 hours. The reaction mixture was then cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (magnesium sulfate), and concentrated to give a yellow oil. Purification by flash chromatography, eluting with ethyl acetate/hexanes, and recrystallization (ethyl acetate/hexanes) provided the 0.5 g of the title compound as yellow crystals, m.p. 150° C.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customPurification by flash chromatography
  8. washeluting with ethyl acetate/hexanes, and recrystallization (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8c8cc36736d548d3825fe289d5cd78a8
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

Loading…