2,6-Difluoro-3-nitrobenzoyl chloride → (2,6-difluoro-3-nitrophenyl)(5-iodo-1H-pyrrolo[2,3-b]pyridin-3-yl)methanone

HRID 60114Notes

Reaction equation

HRID 60114 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[Cl-].[Cl-].[Cl-].[Al+3].[F:15][C:16]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[C:21]([F:28])[C:17]=1[C:18](Cl)=[O:19]>[N+](C)([O-])=O>[F:15][C:16]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[C:21]([F:28])[C:17]=1[C:18]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([I:1])[CH:3]=2)[NH:8][CH:9]=1)=[O:19]

Participants

5

Reactant 3

HCID 27817562,6-Difluoro-3-nitrobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 242292145-Iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 58368945(2,6-difluoro-3-nitrophenyl)(5-iodo-1H-pyrrolo[2,3-b]pyridin-3-yl)methanoneYield 60.2%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

In a reaction vial, 5-iodo-1H-pyrrolo[2,3-b]pyridine (43, 1.00 g, 4.10 mmol) is mixed with 22 mL of nitromethane and aluminum trichloride (3.28 g, 24.6 mmol) is added. The reaction is stirred at room temperature for 1 hour and 2,6-difluoro-3-nitro-benzoyl chloride (44, 1.36 g, 6.15 mmol) is added. The reaction is heated at 45° C. for 93 hours, then quenched with addition of methanol. The resulting precipitate is collected by filtration to provide the desired compound (45, 1.06 g).

Workup

  1. additionis added
  2. temperatureThe reaction is heated at 45° C. for 93 hours
  3. customquenched with addition of methanol
  4. filtrationThe resulting precipitate is collected by filtration

Sources & evidence

ORD record
ord-782eadf38732454696f9145acdc86ea2
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Reaction notes

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