Triacetoxyperiodinane → HCID 86618123, compound

HRID 2381067Notes

Reaction equation

HRID 2381067 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH:23]1([O:28][C:29]2[C:30]([O:52][CH3:53])=[CH:31][CH:32]=[C:33]3[C:38]=2[N:37]([CH2:39][CH2:40][OH:41])[C:36](=[O:42])[CH:35]=[C:34]3[NH:43][C:44]2[C:49]([Cl:50])=[CH:48][N:47]=[CH:46][C:45]=2[Cl:51])[CH2:27][CH2:26][CH2:25][CH2:24]1>C(Cl)Cl>[CH:23]1([O:28][C:29]2[C:30]([O:52][CH3:53])=[CH:31][CH:32]=[C:33]3[C:38]=2[N:37]([CH2:39][CH:40]=[O:41])[C:36](=[O:42])[CH:35]=[C:34]3[NH:43][C:44]2[C:45]([Cl:51])=[CH:46][N:47]=[CH:48][C:49]=2[Cl:50])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 24851913HCID 24851913, compound

Product 1

HCID 86618123HCID 86618123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (933 mg, 2.2 mmol) was added to a solution of 8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-1-(2-hydroxyethyl)-7-methoxyquinolin-2(1H)-one (500 mg, 1.08 mmol, Example 9) and CH2Cl2 (30 mL) at 0° C. After 30 min, the mixture was allowed to warm to rt. When the starting material was consumed, the reaction was diluted with dichloromethane (25 mL), washed with aq. NaOH (20 mL×2), and then washed with water (20 mL). The organic layer was dried, filtered, concentrated, and purified by silica gel chromatography (1:2→1:1; ethyl acetate:petroleum ether) to give 2-(8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde: MS (ESI): 462.2.

Workup

  1. customWhen the starting material was consumed
  2. additionthe reaction was diluted with dichloromethane (25 mL)
  3. washwashed with aq. NaOH (20 mL×2)
  4. washwashed with water (20 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (1:2→1:1; ethyl acetate:petroleum ether)

Sources & evidence

ORD record
ord-e8ce781aa86a4f3190e94dc4d5b60078
Source dataset
uspto-grants-2012_09
Patent number
US08258154B2

Reaction notes

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