Triethylamine → (E)-4-fluoro-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}benzamide

HRID 1821318Notes

Reaction equation

HRID 1821318 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[N:2]1.C(N(CC)CC)C.[F:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[F:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2/[CH:11]=[CH:10]/[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[O:32])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 678794-Fluorobenzoyl chlorideHCID 69001756HCID 69001756, compound

Product 1

HCID 69002865(E)-4-fluoro-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}benzamideYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-2-[2-(1H-indazol-3-yl)vinyl]phenylamine (60 mg, 0.26 mmol) obtained in Example 2 was dissolved in THF (1.5 mL) and the solution was added with triethylamine (71 μL, mmol) and p-fluorobenzoylchloride (45 μL, 0.38 mmol), followed by stirring at room temperature for 30 minutes. Further, the reaction mixture was added with potassium carbonate and stirred for a while. Then, the solid precipitated by adding water to the mixture was collected by filtration and the solid was triturated in ethanol to obtain Compound 3 (57 mg, 62%).

Workup

  1. stirringstirred for a while
  2. customThen, the solid precipitated
  3. additionby adding water to the mixture
  4. filtrationwas collected by filtration
  5. customthe solid was triturated in ethanol

Sources & evidence

ORD record
ord-87f8b1a10d514e87919b0d91e3f91545
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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