HCID 22055276, compound → HCID 22055268, compound

HRID 1829927Notes

Reaction equation

HRID 1829927 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:8]=1[C:9]([NH2:11])=[O:10]>CC(O)=O.CCOC(C)=O.[Fe]>[NH2:16][C:13]1[CH:14]=[CH:15][C:7]([O:6][CH2:5][C:4]2[CH:19]=[CH:20][CH:21]=[C:2]([F:1])[CH:3]=2)=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10]

Participants

4

Reactant 1

HCID 22055276HCID 22055276, compound

Product 1

HCID 22055268HCID 22055268, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22609514Ethyl acetate acetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 14A (162 mg, 0.56 mmol) and Fe powder (249 mg, 4.46 mmol) in HOAc/EtOAc (1/1) (2.4 ml) was heated at 70° C. for 2.5 h. The mixture was cooled to rt, filtered through a 1″ celite pad and rinsed with HOAc/EtOAc (1/1) (4×8 ml). The filtrate was concentrated in vacuo. The residue was diluted with 1N NaOH (25 ml), extracted with EtOAc (2×60 ml) and the combined EtOAc extracts were washed with brine (1×20 ml), dried (MgSO4), filtered and concentrated in vacuo to give 14B (123.8 mg, 67% pure).

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through a 1″ celite pad
  3. washrinsed with HOAc/EtOAc (1/1) (4×8 ml)
  4. concentrationThe filtrate was concentrated in vacuo
  5. additionThe residue was diluted with 1N NaOH (25 ml)
  6. extractionextracted with EtOAc (2×60 ml)
  7. washthe combined EtOAc extracts were washed with brine (1×20 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab143dde2af9493faf4e4ee286f3f388
Source dataset
uspto-grants-2006_06
Patent number
US07064203B2

Reaction notes

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