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

HRID 2423185Notes

Reaction equation

HRID 2423185 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:5][C:4]=1[O:21][CH2:22][CH2:23][NH:24][C:25](=O)[CH3:26].P(Cl)(Cl)(Cl)=O>C(#N)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:13])=[O:14])=[C:5]2[C:25]([CH3:26])=[N:24][CH2:23][CH2:22][O:21][C:4]=12

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67243162N-(2-{[6-methoxy-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)acetamide2×

Product 1

HCID 672416206-Methoxy-1-methyl-8-(phenylsulfonyl)-3,8-dihydro-4H-[1,4]oxazepino[6,7-e]indoleYield 1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To N-(2-{[6-methoxy-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)acetamide (Intermediate 33, 0.10 g, 2.7 mmol) dissolved in acetonitrile (150 mL), phosphoryl chloride (2 mL) was added and the reaction mixture was heated at reflux for 5 days. The solvent was removed under reduced pressure and the crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (0.010 g). MS m/z 371 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 5 days
  3. customThe solvent was removed under reduced pressure
  4. customthe crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN)

Sources & evidence

ORD record
ord-84a140d0bbed43bc9ff51eb252453158
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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