HCID 57163122, compound → HCID 18462014, compound

HRID 2303930Notes

Reaction equation

HRID 2303930 reaction equation
[Br:1][CH2:2][CH2:3][CH:4]=[C:5]1[C:11]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][C:7]2[N:18]=[CH:19][CH:20]=[CH:21][C:6]1=2>C(O)C.C(O)(=O)C.[Pd]>[Br:1][CH2:2][CH2:3][CH2:4][CH:5]1[C:11]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][C:7]2[N:18]=[CH:19][CH:20]=[CH:21][C:6]1=2

Participants

5

Reactant 1

HCID 57163122HCID 57163122, compound

Product 1

HCID 18462014HCID 18462014, compoundYield 29.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of the product of step 2 (160 mg) in ethanol (3 ml) and acetic acid (1 ml) were added 10% Pd—C (79 mg) was stirred under hydrogen (under a balloon) at room temperature for 24 hour. The mixture was filtered through the celite and distilled off under reduced pressure. The residue was purified by preparative thin layer chromatography eluting with ethyl acetate-hexane (1:2) to give 5-(3-bromopropyl)-5,11-dihydro-7-methoxypyrido[2,3-c][1]benzoxepine (48 mg).

Workup

  1. filtrationThe mixture was filtered through the celite
  2. distillationdistilled off under reduced pressure
  3. customThe residue was purified by preparative thin layer chromatography
  4. washeluting with ethyl acetate-hexane (1:2)

Sources & evidence

ORD record
ord-1ae77716dd154894950559978d62f8e4
Source dataset
uspto-grants-2002_08
Patent number
US06433165B1

Reaction notes

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