1-Propanol → HCID 59376458, compound

HRID 1694846Notes

Reaction equation

HRID 1694846 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:22])[C:12](=[O:20])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:5]=1Br.[CH:32]([B-](F)(F)F)=[CH2:33].[K+].CCN(CC)CC.C(O)CC>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:22])[C:12](=[O:20])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:5]=1[CH:32]=[CH2:33]

Participants

7

Reactant 4

HCID 10311-PropanolHCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 67279065HCID 67279065, compound

Product 1

HCID 59376458HCID 59376458, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Procedure

Methyl-2-bromo-4-{3-oxo-3-(phenylamino)-2-[(phenylamino)carbonyl]propyl}benzoate (0.15 g, 0.312 mmol), Pd(dppf)Cl2(0.012 g, 0.02 mmol), potassium vinyltrifluoroborate (0.42 g, 0.312 mmol) were placed in a sealed tube and purge with argon 3×. Et3N (0.13 mL, 0.935 mmol) and n-PrOH (4.0 mL) were then added and the tube was placed in an oil bath at 100° C. for 3 h. The reaction was cool to room temperature and water was added. After extraction with ethyl acetate 3×, dried over Na2SO4, filter and concentrate. The residue was then purified by column chromatography to provide methyl-2-ethenyl-4-{3-oxo-3-(phenylamino)-2-[(phenylamino)carbonyl]propyl}benzoate. MS: Cal'd (MH+) 429, exp (MH+) 429.

Workup

  1. custompurge with argon 3×
  2. extractionAfter extraction with ethyl acetate 3×
  3. dry with materialdried over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-05c49f40709343908e7e078ad6a8817d
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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