Selenium Dioxide → HCID 21034920, compound

HRID 1833122Notes

Reaction equation

HRID 1833122 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:3]=1[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:7][N:6]=1.[Se](=O)=[O:31]>C(OCC)(=O)C>[CH2:22]([O:21][C:19]([C:8]1[C:9]2[C:14](=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=2)[C:5]([C:4](=[O:31])[C:3]2[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:2]=2[F:1])=[N:6][CH:7]=1)=[O:20])[CH3:23]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 22048390HCID 22048390, compound

Product 1

HCID 21034920HCID 21034920, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The above 1-(2-fluoro-5-methoxybenzyl)-4-ethoxycarbonyl-6,7-dimethoxyisoquinoline was dissolved in ethyl acetate (25 ml) and selenium dioxide was added (723 mg). The mixture was refluxed for 1 hr until all starting material was consumed. The solution was filtered through a layer of Celite and the filtrate was concentrated. The residue was purified through a flash column chromatography using hexane and ethyl acetate (3/1 ratio) to give 1-(2-fluoro-5-methoxybenzoyl-6,7-dimethoxyisoquinoline-4-caboxylic acid ethyl ester (1.28 g). This ester (200 mg, 0.48 mmol) was suspended in 10 ml of methanol and 1N sodium hydroxide solution (2.0 ml) was added. The mixture was refluxed for 30 minutes and the solution was loaded to a preparative HPLC for purification to give 1-(2-Fluoro-5-methoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid (138 mg). ES-MS calcd for C20H16FNO6 (m/e) 385.36, obsd 386.2 (M+H).

Workup

  1. temperatureThe mixture was refluxed for 1 hr until all starting material
  2. customwas consumed
  3. filtrationThe solution was filtered through a layer of Celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified through a flash column chromatography

Sources & evidence

ORD record
ord-62c254e470c1420f88e1cac50dfa0dd8
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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