Pyridine → 2-Acetoxy-4-(3-bromo-4,5-dimethoxyphenyl)-7-dimethylamino-chroman

HRID 1454001Notes

Reaction equation

HRID 1454001 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[CH:17][C:18]([N:22]([CH3:24])[CH3:23])=[CH:19][CH:20]=3)[O:15][CH:14]([OH:25])[CH2:13]2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].CN(C1C=CC=CN=1)C.N1C=CC=CC=1.[C:41](OC(=O)C)(=[O:43])[CH3:42]>ClCCl>[C:41]([O:25][CH:14]1[CH2:13][CH:12]([C:4]2[CH:5]=[C:6]([O:10][CH3:11])[C:7]([O:8][CH3:9])=[C:2]([Br:1])[CH:3]=2)[C:21]2[C:16](=[CH:17][C:18]([N:22]([CH3:23])[CH3:24])=[CH:19][CH:20]=2)[O:15]1)(=[O:43])[CH3:42]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 100014744-(3-Bromo-4,5-dimethoxyphenyl)-7-dimethylamino-2-hydroxy-chroman

Product 1

HCID 102532012-Acetoxy-4-(3-bromo-4,5-dimethoxyphenyl)-7-dimethylamino-chroman

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(3-bromo-4,5-dimethoxyphenyl)-7-dimethylamino-2-hydroxy-chroman (9 mg, 0.022 mmol), dimethylamino-pyridine (catalytic) and pyridine (0.1 ml) in dichloromethane at 0° C. was added acetic anhydride (0.05 ml). The mixture was stirred overnight at room temperature. To the mixture was added ice and the mixture was extracted with dichloromethane. The extract was washed with 1N HCl, saturated NaHCO3 and saturated sodium chloride solution, dried and the solvent was evaporated. The title compound was obtained upon chromatography of the crude material over a bond-elute (hexane:ethyl acetate=9:1 and 4:1 as eluent) (6.0 mg; 61%). 1H NMR (CD3OD): 6.99 (d, J=1.9 Hz), 6.86 (broad signal) and 6.85 (d, J=1.8 Hz) (2H), 6.72 (d, J=8.8 Hz) and 6.54 (d, J=8.5 Hz) (1H), 6.47 (t, J=2.3 Hz) and 6.42 (dd, J=2.2, 9.2 Hz) (1H), 6.35 (overlapping dd, J=2.5, 8.7 Hz) (1H), 6.26 (d, J=2.3 Hz) and 6.22 (d, J=2.5 Hz) (1H), 4.14 (overlapping dd, J=6.0, 11.9 Hz; 1H), 3.76-3.80 (s, 6H), 2.87 and 2.91 (s each, 6H), 2.40-2.45 and 2.11-2.32 (m each; 2H), 2.08 and 1.79 (s each, 3H).

Workup

  1. additionTo the mixture was added ice
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe extract was washed with 1N HCl, saturated NaHCO3 and saturated sodium chloride solution
  4. customdried
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-14c6988cb1824582a79feef0729e9733
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

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