1,4-Dioxane → HCID 67445972, compound

HRID 1960139Notes

Reaction equation

HRID 1960139 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:23]([Cl:24])=[CH:22][C:10]3[NH:11][C:12]([CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=4)=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.[O:31]1CCOCC1>O=[Mn]=O>[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:23]([Cl:24])=[CH:22][C:10]3[NH:11][C:12]([C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=4)=[O:31])=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 67448110HCID 67448110, compound

Product 1

HCID 67445972HCID 67445972, compound

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Conditions

Temperature
70 °C

Procedure

To a solution of compound 14-1 (270 mg, 0.57 mmol) in dioxane was added MnO2 (100 mg, 1.1 mmol). The reaction was allowed to stir at 70° C. for 48 h. The reaction mixture was filtered over a bed of Celite™ and washed with copious amounts of EtOAc. The product was concentrated in vacuo, and then purified on ISCO (EtOAc/Hexanes=1/1) to give the title compound 14-2 as a pale yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered over a bed of Celite™
  2. washwashed with copious amounts of EtOAc
  3. concentrationThe product was concentrated in vacuo
  4. custompurified on ISCO (EtOAc/Hexanes=1/1)

Sources & evidence

ORD record
ord-e7de6178e9e0482f8b1039e40296e083
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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