Triphenylphosphine → HCID 59410088, compound

HRID 2404906Notes

Reaction equation

HRID 2404906 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[CH:4][C:3]=1[NH:15][C:16](=O)[C:17]([F:20])([F:19])[F:18].C1C(=O)N(Br)C(=O)C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[F:11][C:10]([F:13])([F:12])[C:9]([NH:8][C:5]1[CH:4]=[C:3]2[C:2]([CH:1]=[C:16]([C:17]([F:20])([F:19])[F:18])[NH:15]2)=[CH:7][CH:6]=1)=[O:14]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 59410048HCID 59410048, compound

Product 1

HCID 59410088HCID 59410088, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of N,N′-(4-methyl-1,3-phenylene)bis(2,2,2-trifluoroacetamide) (1.02 g, 3.25 mmol), NBS (0.80 g, 4.5 mmol) in CCl4 (6 mL) was stirred overnight at room temperature under irradiation of a 300 W lamp. The precipitate formed was collected by filtration and washed with CCl4. The crude residue was taken up in dry toluene (9.7 mL) in the presence of PPh3 (1.3 g, 4.96 mmol) and stirred at 60° C. for 16 h. The phosphonium precipitate was collected by filtration, then dissolved in dry DMF (10 mL) and stirred at 165° C. until complete conversion to the product (6.5 h). The solvent was removed in vacuo and the residue obtained was purified by silica gel column chromatography (5-25% AcOEt in hexanes) to obtain 2,2,2-trifluoro-N-(2-(trifluoromethyl)-1H-indol-6-yl)acetamide (243 mg, 25%). LC/MS: m/z 297.3 (M+H)+ at 1.68 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed with CCl4
  4. stirringstirred at 60° C. for 16 h
  5. filtrationThe phosphonium precipitate was collected by filtration
  6. dissolutiondissolved in dry DMF (10 mL)
  7. stirringstirred at 165° C. until complete conversion to the product (6.5 h)
  8. customThe solvent was removed in vacuo
  9. customthe residue obtained
  10. customwas purified by silica gel column chromatography (5-25% AcOEt in hexanes)

Sources & evidence

ORD record
ord-1fd5a86ee7524682bf38c08d114eafb9
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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