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

HRID 2423194Notes

Reaction equation

HRID 2423194 reaction equation
[CH3:1][CH:2]([CH3:27])[C:3]([NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH:13]=[CH:12]2)=O.P(Cl)(Cl)(Cl)=O>C(#N)C>[CH:2]([C:3]1[C:10]2=[C:11]3[C:15](=[CH:16][CH:17]=[C:9]2[O:8][CH2:7][CH2:6][N:5]=1)[N:14]([S:18]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)(=[O:20])=[O:19])[CH:13]=[CH:12]3)([CH3:1])[CH3:27]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 672406902-Methyl-N-(2-{[1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)propanamide2×

Product 1

HCID 672422461-Isopropyl-8-(phenylsulfonyl)-3,8-dihydro-4H-[1,4]oxazepino[6,7-e]indoleYield 98.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2-methyl-N-(2-{[1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)propanamide (Intermediate 37, 0.13 g, 0.33 mmol) in acetonitrile (200 mL) was phosphoryl chloride (2.5 mL) added and the reaction mixture was heated at reflux for 20 hours. The reaction mixture was evaporated to give the title compound (120 mg). MS m/z 369 [M+H]+.

Workup

  1. additionadded
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 20 hours
  4. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-a3306c32e7ff4aa0941f0c85e9aaca0b
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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