Phosphorus oxybromide → HCID 86595467, compound

HRID 523694Notes

Reaction equation

HRID 523694 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](O)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].P(Br)(Br)([Br:29])=O>C1(C)C=CC=CC=1>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:29])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178450857HCID 178450857, compound

Product 1

HCID 86595467HCID 86595467, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7-cyclohexyloxy-1,4-dihydroxy-isoquinoline-3-carboxylic acid butyl ester (Compound A-74 c1) (1.3 g) and phosphorus oxybromide (1.35 g) in anhydrous toluene (25 ml) was heated in a microwave reactor (sealed tube) at 130° C. for 15 min. After cooling, reaction mixture was concentrated. The residue was treated with saturated sodium bicarbonate aqueous solution (100 ml) and stirred at room temperature for 20 min. Extracted with ethyl acetate. Organic layer was washed with water, brine, dried over magnesium sulfate, filtered, and concentrated to give the title compound (1.2 g). MS-(+)-ion M+1=422.12, 424.12.

Workup

  1. temperaturewas heated in a microwave reactor
  2. custom(sealed tube) at 130° C. for 15 min
  3. temperatureAfter cooling
  4. customreaction mixture
  5. concentrationwas concentrated
  6. additionThe residue was treated with saturated sodium bicarbonate aqueous solution (100 ml)
  7. extractionExtracted with ethyl acetate
  8. washOrganic layer was washed with water, brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-a5eda939d2024b4ab969d4a8b6320183
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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