Ethyl 4-[[3,5-bis(trimethylsilyl)benzoyl]amino]-2-fluorocinnamate → (E)-Ethyl 3-[4-[[3,5-bis(trimethylsilyl)benzoyl]amino]-2,5-difluorophenyl]-2-butenoate

HRID 2265097Notes

Reaction equation

HRID 2265097 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5](/[C:9](/[CH3:16])=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([F:17])[CH:3]=1.[CH3:18][Si:19]([CH3:48])([CH3:47])[C:20]1[CH:21]=[C:22]([CH:40]=[C:41]([Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:42]=1)[C:23](NC1C=CC(C=CC(OCC)=O)=C(F)C=1)=[O:24]>>[CH3:44][Si:43]([CH3:46])([CH3:45])[C:41]1[CH:40]=[C:22]([CH:21]=[C:20]([Si:19]([CH3:48])([CH3:47])[CH3:18])[CH:42]=1)[C:23]([NH:1][C:2]1[C:7]([F:8])=[CH:6][C:5](/[C:9](/[CH3:16])=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([F:17])[CH:3]=1)=[O:24]

Participants

3

Reactant 2

HCID 68484203Ethyl 4-[[3,5-bis(trimethylsilyl)benzoyl]amino]-2-fluorocinnamateHCID 86644278(E)-Ethyl 3-(4-amino-2,5-difluorophenyl)-2-butenoate

Product 1

HCID 86644279(E)-Ethyl 3-[4-[[3,5-bis(trimethylsilyl)benzoyl]amino]-2,5-difluorophenyl]-2-butenoateYield 46%

Procedure

BTMB (800 mg) and Compound 10a (869 mg) were reacted in the same manner as Compound 2b was synthesized. After the reaction was over, the reaction mixture was separated with ethyl acetate and water. The organic layer was washed once with water and once with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (5% ethyl acetate/n-hexane) to obtain Compound 10b (674 mg, 46%) as a light yellow solid.

Workup

  1. customwas synthesized
  2. customwas separated with ethyl acetate and water
  3. washThe organic layer was washed once with water and once with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (5% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-8891bfeb29be478581e150da1efe3786
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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