Diethyl Ether → t-butyl N-(2-fluoro-6-cinnamylbenzyl)carbamate

HRID 2390044Notes

Reaction equation

HRID 2390044 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13](I)[C:3]=1[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].C(O[CH2:22][CH:23]=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=O)C.C(OCC)C>CN(C=O)C.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]>[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:22][CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:3]=1[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 76603-Phenyl-2-propen-1-yl acetateHCID 59323180t-butyl N-(2-fluoro-6-iodobenzyl)carbamate

Product 1

HCID 68521872t-butyl N-(2-fluoro-6-cinnamylbenzyl)carbamateYield 52%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Under an argon atmosphere, 300 mg of t-butyl N-(2-fluoro-6-iodobenzyl)carbamate, 0.29 mL of cinnamyl acetate, 1.28 mL of bistributyltin, and 70 mg of PdCl2(dppf)2 were dissolved in 2.5 mL of DMF, followed by stirring at 120° C. for 2 hours. After completion of the reaction, to the reaction liquid was added diethyl ether, followed by filtration through Celite, and to the filtrate was added water, followed by extraction with diethyl ether. Then, the organic layer was washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using PLC (n-hexane:ethyl acetate=3:1) to obtain 121 mg (yield 52%) of a title compound as a yellow solid.

Workup

  1. customAfter completion of the reaction
  2. customto the reaction liquid
  3. filtrationfollowed by filtration through Celite
  4. additionto the filtrate was added water
  5. extractionfollowed by extraction with diethyl ether
  6. washThen, the organic layer was washed with an aqueous sodium bicarbonate solution and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue obtained
  10. customwas purified

Sources & evidence

ORD record
ord-4268909112f244f291f124e1d3b18aa5
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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