p-(Trifluoromethoxy)benzaldehyde → 6-Bromo-4-hydroxy-3-(4-(trifluoromethoxy)benzyl)quinolin-2(1H)-one

HRID 926531Notes

Reaction equation

HRID 926531 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[OH:13].ClC1C2C(=CC=C(C(C3N(C)C(C)=NC=3)O)C=2)N=C(OC)C=1CC1C=NC(C(F)(F)F)=CC=1.[F:47][C:48]([F:59])([F:58])[O:49][C:50]1[CH:57]=[CH:56][C:53]([CH:54]=O)=[CH:52][CH:51]=1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([CH2:54][C:53]1[CH:56]=[CH:57][C:50]([O:49][C:48]([F:47])([F:58])[F:59])=[CH:51][CH:52]=1)=[C:5]2[OH:13]

Participants

6

Reactant 4

HCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 70849Hantzsch esterHCID 546894466-Bromo-4-hydroxyquinolin-2(1H)-oneHCID 118005815(4-Chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanol

Product 1

HCID 1180062566-Bromo-4-hydroxy-3-(4-(trifluoromethoxy)benzyl)quinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a dark solution of 6-bromo-4-hydroxyquinolin-2(1H)-one (1.0 g, 4.25 mmol, Intermediate 45: step a) and 4-(trifluoromethoxy)benzaldehyde (0.67 mL, 4.67 mmol) in pyridine (7.5 mL) was added diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (1.08 g, 4.25 mmol). The resulting mixture was warmed with stirring in a 100° C. oil bath for a period of 5 hours. After cooling to room temperature, the solvent was removed under reduced pressure and the residue diluted with acetonitrile. The semi-solid mixture was sonicated and filtered, rinsing further with acetonitrile, to provide the title compound as a white solid.

Workup

  1. temperatureThe resulting mixture was warmed
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was removed under reduced pressure
  4. additionthe residue diluted with acetonitrile
  5. customThe semi-solid mixture was sonicated
  6. filtrationfiltered
  7. washrinsing further with acetonitrile

Sources & evidence

ORD record
ord-dd30c35afa88437591696d5d89a5805e
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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