Pyridine → HCID 89487982, compound

HRID 570761Notes

Reaction equation

HRID 570761 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([Br:18])[C:3]=1[NH:19][C:20](=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][CH3:28])[C:22]=1[O:29][CH3:30].N1C=CC=CC=1.Cl.[C:39](Cl)(=[O:46])[C:40]1[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=1>CN(C)C1C=CN=CC=1.C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:9]([F:12])([F:10])[F:11])[C:13]([F:14])([F:15])[F:16])[CH:5]=[C:4]([Br:18])[C:3]=1[NH:19][C:20]([C:21]1[C:22]([O:29][CH3:30])=[C:23]([N:27]([CH3:28])[C:39]([C:40]2[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=2)=[O:46])[CH:24]=[CH:25][CH:26]=1)=[O:31]

Participants

6

Reactant 3

HCID 1049PyridineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 89492756HCID 89492756, compound

Product 1

HCID 89487982HCID 89487982, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-methoxy-3-(methylamino)benzamide (0.600 g, 1.03 mmole), 4-dimethylaminopyridine (0.006 g) and pyridine (0.334 ml, 0.327 g, 4 mmole) in THF (11.4 ml) was treated with isonicotinoyl chloride hydrochloride (0.386 g, 2 mmole). The resulting white suspension was heated under reflux for 0.5 hour. The reaction mixture was filtered and the filtrate evaporated under reduced pressure. The residue was taken up in aqueous saturated sodium bicarbonate solution. The product was extracted with ethyl acetate and the organic phase was washed with brine and dried over sodium sulfate. The crude product was purified by column chromatography over silica gel using ethyl acetate 50%-cyclohexane 50% to yield the title compound corresponding to compound No. G14 of table G.

Workup

  1. temperatureThe resulting white suspension was heated
  2. temperatureunder reflux for 0.5 hour
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate evaporated under reduced pressure
  5. extractionThe product was extracted with ethyl acetate
  6. washthe organic phase was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customThe crude product was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-0249feaee85643998110e42784d6142a
Source dataset
uspto-grants-2015_05
Patent number
US09023873B2

Reaction notes

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