Phosphorus oxybromide → HCID 89812986, compound

HRID 1481203Notes

Reaction equation

HRID 1481203 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]([S: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]([S: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 178450861HCID 178450861, compound

Product 1

HCID 89812986HCID 89812986, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 7-cyclohexylsulfanyl-1,4-dihydroxy-isoquinoline-3-carboxylic acid butyl ester (2.95 g, 7.87 mmol) in toluene (40 mL) was added POBr3 (3.38 g, 11.8 mmol) was refluxed for 3 h. Reaction mixture was cooled to 0° C. and quenched with saturated NaHCO3 aqueous solution (100 mL). It was stirred for 15 min., and then was extracted with EtOAc. Organic layer was washed with brine, dried over MgSO4, filtered and concentrated to provide the title compound 2.55 g (5.82 mmol), which was used directly to the next reaction without further purification. 1H NMR (200 MHz) CDCl3, δ in ppm: 11.85 (s, 1H), 8.23 (d, J=8.8 Hz, 1H), 8.05 (s, 1H), 7.65 (d, J=8.5 Hz, 1H), 4.47 (t, J=7.0 Hz, 2H), 3.46 (br S, 1H), 2.10 (br m, 2H), 1.85-1.42 (m, 12H), 0.99 (t, J=7.1 Hz, 3H).

Workup

  1. temperaturewas refluxed for 3 h
  2. customReaction mixture
  3. customquenched with saturated NaHCO3 aqueous solution (100 mL)
  4. extractionwas extracted with EtOAc
  5. washOrganic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0670db69a61849de97a30cea31bef1bd
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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