Phosphorus oxychloride → 1-methyl-8-(phenylsulfonyl)-3,8-dihydro-4H-[1,4]oxazepino[6,7-e]indole

HRID 2423176Notes

Reaction equation

HRID 2423176 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][NH:22][C:23](=O)[CH3:24])=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[CH3:24][C:23]1[C:14]2=[C:13]3[C:18](=[CH:17][CH:16]=[C:15]2[O:19][CH2:20][CH2:21][N:22]=1)[N:10]([S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])[CH:11]=[CH:12]3

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67242197N-(2-{[1-(Phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)acetamide2×

Product 1

HCID 250545001-methyl-8-(phenylsulfonyl)-3,8-dihydro-4H-[1,4]oxazepino[6,7-e]indoleYield 104.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To N-(2-{[1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)acetamide (Intermediate 25, 5.0 g, 14 mmol) in acetonitrile (7.5 L) was phosphoryl chloride (100 mL) added and the reaction mixture was heated at reflux overnight. The reaction mixture was allowed to cool to room temperature and the solvent was removed under reduced pressure to give the crude material of the title compound (5.0 g). A small amount of the crude material was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (12 mg). MS m/z 341 [M+H]+.

Workup

  1. additionadded
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux overnight
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-29889e57b9914fbc8bc564e3acfbf9d5
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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