Methanol → HCID 86600131, compound

HRID 1453991Notes

Reaction equation

HRID 1453991 reaction equation
[NH2:1][CH:2]1[N:26]([C:27]#[N:28])[CH:5]2[CH:6]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([Br:25])[CH:16]=3)[CH:7]=[C:8]3[C:13]([O:12][C:11](=[O:14])[CH:10]=[CH:9]3)=[C:4]2[O:3]1.[C:29](=O)([O-])[O-].[Cs+].[Cs+].CI.CO>CC(C)=O.ClCCl>[NH2:1][CH:2]1[N:26]([C:27]#[N:28])[CH:5]2[CH:6]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([Br:25])[CH:16]=3)[CH:7]=[C:8]3[C:13]([O:12][C:11](=[O:14])[C:10]([CH3:29])=[CH:9]3)=[C:4]2[O:3]1

Participants

7

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86600130HCID 86600130, compound

Product 1

HCID 86600131HCID 86600131, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

2-amino-4-(3-bromo-4,5-dimethoxyphenyl)-3-cyano-8-oxo-4H-oxazolo[4,5-h]chromene (335 mg, 0.75 mmol) and cesium carbonate (270 mg, 0.83 mmol) were diluted in dry acetone (10 mL). Methyl iodide (2M solution in tert-butyl methyl ether, 415 μL, 0.83 mmol) was added and the reaction was stirred at room temperature overnight. Solvent was removed in vacuo and the residue was partitioned between water (20 mL) and EtOAc (60 mL). The aqueous layer was extracted with EtOAc (2×50 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated to a yellow solid. The product was isolated by flash chromatography using a 25S SiO2 system by Biotage, Inc., Charlottesville, Va., using 0 to 1% methanol in dichloromethane to yield 292 mg (85%) 2-amino-4-(3-bromo-4,5-dimethoxyphenyl)-3-cyano-7-methyl-8-oxo-4H-oxazolo[4,5-h]chromene as a light yellow solid. 1H NMR (Acetone-d6) 7.04-6.93 (m, 4H), 6.49 (brs, 2H), 4.83 (s, 1H), 3.86 (s, 3H), 3.76 (s, 3H), 3.39 (s, 3H).

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue was partitioned between water (20 mL) and EtOAc (60 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow solid
  7. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-8fd810a8548c4472b2e3550dcc6d40b4
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

Loading…