HCID 57651816, compound → HCID 57651817, compound

HRID 907423Notes

Reaction equation

HRID 907423 reaction equation
[N:1]([C:4]1[N:9]=[C:8]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])[C:7](Cl)=[C:6]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:5]=1[F:23])=[N+]=[N-]>[Pd].CCO>[NH2:1][C:4]1[C:5]([F:23])=[C:6]([O:17][CH2:18][C:19]([F:21])([F:22])[F:20])[CH:7]=[C:8]([O:10][CH2:11][C:12]([F:15])([F:13])[F:14])[N:9]=1

Participants

4

Reactant 1

HCID 57651816HCID 57651816, compound

Product 1

HCID 57651817HCID 57651817, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A 350 mL stainless steel pressure reactor equipped with a mechanical stirrer was charged with 6-azido-2,4-bis(2,2,2-trifluoroethoxy)-3-chloro-5-fluoropyridine (14.0 g, 38.0 mmol), EtOH (50 mL), and palladium on carbon (10%, 4.0 g). The reactor was sealed and pressurized with H2 (500 psi). The pressurized reactor was heated to 100° C. After 18 h the pressurized reactor was cooled to ambient temperature. A GC analysis indicated all the starting material was consumed. The reaction was filtered and the volatiles evaporated to afford the crude product as a brown oil. The brown oil was purified by column chromatography (SiO2, hexane/EtOAc) to afford the product as a brown crystalline solid (7.29 g, 62% yield): mp 43-45° C.; 1H NMR (CDCl3) δ 5.84 (d, J=4.1 Hz, 1H), 5.85-4.56 (q, J=8.5, 2H), 4.49-4.37 (m, 4H); GC-MS (EI, 70 eV) m/z (% relative intensity) 308 (100), 289 (26), 239 (74).

Workup

  1. customA 350 mL stainless steel pressure reactor equipped with a mechanical stirrer
  2. customThe reactor was sealed
  3. temperatureAfter 18 h the pressurized reactor was cooled to ambient temperature
  4. customwas consumed
  5. filtrationThe reaction was filtered
  6. customthe volatiles evaporated
  7. customto afford the crude product as a brown oil
  8. customThe brown oil was purified by column chromatography (SiO2, hexane/EtOAc)

Sources & evidence

ORD record
ord-7f776a7e144a4ea29fda4fc8a94c8e02
Source dataset
uspto-grants-2011_09
Patent number
US08013154B2

Reaction notes

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