HCID 22055265, compound → HCID 22055293, compound

HRID 1829925Notes

Reaction equation

HRID 1829925 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][N:8]=1>CC(O)=O.CCOC(C)=O.[Fe]>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][O:6][C:7]1[N:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 22055265HCID 22055265, compound

Product 1

HCID 22055293HCID 22055293, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22609514Ethyl acetate acetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 13A (132 mg, 0.53 mmol) and Fe powder (238 mg, 4.25 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 13B (101.7 mg, 78% pure) which was used in the next step without further purification.

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-f3925866eff647c3b61c9419ce2ca47b
Source dataset
uspto-grants-2006_06
Patent number
US07064203B2

Reaction notes

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