Pyridine → HCID 86707263, compound

HRID 576045Notes

Reaction equation

HRID 576045 reaction equation
N1C=CC=CC=1.CN(C1C=CC=CN=1)C.[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.[F:24][C:25]([F:42])([F:41])[C:26]([N:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([S:37](Cl)(=[O:39])=[O:38])[CH:34]=2)[CH2:29]1)=[O:27]>C(Cl)(Cl)Cl>[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][S:37]([C:33]2[CH:34]=[C:35]3[C:30](=[CH:31][CH:32]=2)[CH2:29][N:28]([C:26](=[O:27])[C:25]([F:42])([F:24])[F:41])[CH2:36]3)(=[O:38])=[O:39])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 97314-FluoroanilineHCID 218852-DimethylaminopyridineHCID 867072642,3-Dihydro-2-(2,2,2-trifluoroacetyl)-1H-isoindole-5-sulfonyl chloride

Product 1

HCID 86707263HCID 86707263, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Pyridine (2.57 mL, 31.9 mmol) and dimethylaminopyridine (195 mg, 1.59 mmol) were added to a solution of 4-fluoroaniline (1.86 g, 16.7 mmol) in chloroform (46 mL) at room temperature and the mixture was cooled in ice. 2-(Trifluoroacetyl)-2,3-dihydro-1 H-isoindole-5-sulfonyl chloride (5.00 g, 15.9 mmol) was added thereto and the mixture was warmed to room temperature and stirred for 15 hr. The reaction mixture was concentrated under reduced pressure and the residue was diluted with ethyl acetate. The mixture was washed with 1 mol/L hydrochloric acid and brine, the organic layer was dried over anhydrous magnesium sulfate, and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was powdered with diethyl ether and collected by filtration to afford the title compound as a pale pink powder (5.85 g).

Workup

  1. temperaturethe mixture was cooled in ice
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washThe mixture was washed with 1 mol/L hydrochloric acid and brine
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationthe desiccant was filtered off
  7. concentrationfollowed by concentration under reduced pressure
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-1a3473361da749be83dd5099d4e2951b
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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