Proton sponge → 6-Methoxy-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

HRID 2423161Notes

Reaction equation

HRID 2423161 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])=[C:5]2[CH2:21][N:22](C)[CH2:23][CH2:24][O:25][C:4]=12.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.ClC(OC(Cl)C)=O>C(Cl)Cl>[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:14])=[O:13])=[C:5]2[CH2:21][NH:22][CH2:23][CH2:24][O:25][C:4]=12

Participants

5

Reactant 3

HCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformateHCID 250573406-Methoxy-2-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

Product 1

HCID 250542356-Methoxy-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indoleYield 10.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 6-methoxy-2-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole (Example 48, 0.030 g, 0.081 mmol), 1,8-Bis(dimethylamino)-naphthalene (0.010 g, 0.048 mmol) and 1-chloroethyl chloroformate (25 mg, 0.18 mmol) were added followed by dry DCM (2 mL). The reaction mixture was stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure and the crude material was dissolved in dry MeOH (3 mL). The reaction mixture was heated at reflux for 2 hours, cooled and the crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (3 mg). MS m/z 359 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe crude material was dissolved in dry MeOH (3 mL)
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 2 hours
  5. temperaturecooled
  6. customthe crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN)

Sources & evidence

ORD record
ord-f7aa2e79c5b543f9b5a4c4bf78ff037b
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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