Isopropanol → HCID 178517028, compound

HRID 926517Notes

Reaction equation

HRID 926517 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].[F:14][C:15]([F:25])([F:24])[C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][N:17]=1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O.C(O)(C)C>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([OH:12])[C:6]([CH2:20][C:19]1[CH:18]=[N:17][C:16]([C:15]([F:25])([F:14])[F:24])=[CH:23][CH:22]=1)=[C:5]2[OH:13]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 70849Hantzsch esterHCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 546894466-Bromo-4-hydroxyquinolin-2(1H)-one

Product 1

HCID 178517028HCID 178517028, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 6-bromo-4-hydroxyquinolin-2(1H)-one (3.2 g, 18.3 mmol, Intermediate 45: step a), 6-(trifluoromethyl)nicotinaldehyde (4.0 g, 16.7 mmol) and diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (4.2 g, 16.7 mmol) in pyridine (34 mL) was heated to 105° C. for 3 hours. The solution was allowed to cool to ambient temperature, resulting in the formation of solid. Minimal isopropanol was added to the mixture and the slurry was stirred for 1 hour, sonicated, and filtered. The filtered solids were rinsed with isopropanol and dried under continuous air flow to provide the title compound as an off-white solid. Additional product was recrystallized from the filtrate, filtered, and rinsed with isopropanol.

Workup

  1. customresulting in the formation of solid
  2. customsonicated
  3. filtrationfiltered
  4. washThe filtered solids were rinsed with isopropanol
  5. customdried under continuous air flow

Sources & evidence

ORD record
ord-20ab0f95149643e4afe75c18c2644d3c
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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