Methyl morpholine oxide → 4-(3-Bromo-4,5-dimethoxyphenyl)-7-methyl-pyrrolo[2,3-h]chroman-2-one

HRID 1454005Notes

Reaction equation

HRID 1454005 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[C:17]4[CH:24]=[CH:23][N:22]([CH3:25])[C:18]4=[CH:19][CH:20]=3)[O:15][CH:14]([OH:26])[CH2:13]2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].C[N+]1([O-])CCOCC1>ClCCl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[C:17]4[CH:24]=[CH:23][N:22]([CH3:25])[C:18]4=[CH:19][CH:20]=3)[O:15][C:14](=[O:26])[CH2:13]2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 103872724-(3-Bromo-4,5-dimethoxyphenyl)-2-hydroxy-7-methyl-pyrrolo[2,3-h]chroman

Product 1

HCID 100019334-(3-Bromo-4,5-dimethoxyphenyl)-7-methyl-pyrrolo[2,3-h]chroman-2-oneYield 20.6%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(3-bromo-4,5-dimethoxyphenyl)-2-hydroxy-7-methyl-pyrrolo[2,3-h]chroman (6 mg; 0.014 mmol), molecular sieves 4A° (20 mg) and 4-methylmorpholin-N-oxide (2 mg; 0.017 mmol ) in dichloromethane (0.5 ml) at 0° C. was added TPAP (0.4 mg). The mixture was stirred at this temperature for 0.5 h and at room temperature for 20 min. It was concentrated and passed through a bond-elute (hexane:ethyl acetate=9:1 and 4:1 as eluents), yielding the title compound (1.2 mg; 20%). 1H NMR (acetone-d6): 7.30 (d, J=3.1 Hz; 1H), 7.21 (dd, J=0.8, 8.4 Hz; 1H), 7.03 (d, J=2.0 Hz; 1H), 6.92 (d, J=8.4 Hz; 1H), 6.87 (dd, J=0.6, 2.1 Hz; 1H), 6.55 (dd, J=0.8, 3.1 Hz; 1H), 4.55 (t, J=5.9 Hz; 1H), 3.86, 3.84, 3.77 (s each, 9H), 3.24 (dd, J=6.4, 15.8 Hz; 1H), 3.13 (dd, J=5.9, 15.8 Hz; 1H).

Workup

  1. concentrationIt was concentrated
  2. washa bond-elute (hexane:ethyl acetate=9:1 and 4:1 as eluents)

Sources & evidence

ORD record
ord-ca7f847e68554e6a97447b4682885042
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

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