Undec-4-ene → HCID 67389573, compound

HRID 906849Notes

Reaction equation

HRID 906849 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7](=O)[CH2:8][C:9](=O)[C:10]([F:14])([F:13])[CH2:11][CH3:12])[O:5][CH:6]=1.[C:17]([CH2:19][C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[F:31])=[O:21])#[N:18].CCCCCCC=CCCC>C1C=CC=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:7]2[N:22]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[F:31])[C:20](=[O:21])[C:19]([C:17]#[N:18])=[C:9]([C:10]([F:14])([F:13])[CH2:11][CH3:12])[CH:8]=2)[O:5][CH:6]=1

Participants

6

Reactant 3

HCID 136496Undec-4-eneHCID 2799809HCID 2799809, compoundHCID 67389092HCID 67389092, compound

Product 1

HCID 67389573HCID 67389573, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-bromo-furan-2-yl)-4,4-difluoro-hexane-1,3-dione (220 mg, 0.75 mmol), and 2-cyano-N-(2,4-difluoro-benzyl)-acetamide (300 mg, 1.4 mmol) in benzene (4 mL) was added 1,8-diaza-bicycle-[5.4.0]-undec-7-ene (60 μL, 0.4 mmol). The red reaction mixture was then heated to reflux. After 3 hours, heating was discontinued and the reaction was allowed to cool to ambient temperature. After stirring at ambient temperature for 16 hours the reaction mixture was diluted with CH2Cl2 and purified by adsorbing the material onto silica gel, loading the resulting solid onto the column and eluting with a gradient from 0% to 30% ethyl acetate/hexane to afford 6-(4-bromo-furan-2-yl)-1-(2,4-difluoro-benzyl)-4-(1,1-difluoro-propyl)-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (188 mg, 54% yield) as a yellow oil. 1H-NMR (400 MHz, CDCl3): δ 7.62 (1H, s), 7.1-7.03 (1H, m), 6.86-6.78 (2H, m), 6.76 (1H, s), 6.64 (1H, s), 5.46 (2H, s), 2.31 (2H, t of q, JH-H=7.6 Hz, JH-F=16.9 Hz), 1.11 (3H, t, J=7.6 Hz).

Workup

  1. customThe red reaction mixture
  2. temperaturewas then heated to reflux
  3. temperatureheating
  4. custompurified
  5. washeluting with a gradient from 0% to 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d8b02c08ed714a44aa8dedadc416c562
Source dataset
uspto-grants-2011_09
Patent number
US08013001B2

Reaction notes

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