Iodopentafluoroethane → HCID 86728475, compound

HRID 1752965Notes

Reaction equation

HRID 1752965 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[O:7])=[C:4]([F:19])[CH:3]=1.[F:20][C:21]([F:27])([F:26])[C:22]([F:25])([F:24])I>CS(C)=O.O.[Cu]>[F:19][C:4]1[CH:3]=[C:2]([C:22]([F:25])([F:24])[C:21]([F:27])([F:26])[F:20])[CH:18]=[CH:17][C:5]=1[C:6]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([O:15][CH3:16])[CH:10]=1)=[O:7]

Participants

6

Reactant 2

HCID 9636IodopentafluoroethaneHCID 86728474HCID 86728474, compound

Product 1

HCID 86728475HCID 86728475, compoundYield 22.3%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 4-bromo-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide (800 mg, 2.46 mmol) and copper (1.6 g, 24.61 mmol) in DMSO (15 mL), in a pressure vessel was bubbled in 1,1,1,2,2-pentafluoro-2-iodo-ethane (4.1 g, 16.47 mmol) The vessel was sealed and heated at 120° C. for 16 hours. The reaction mixture was diluted with water and filtered through a plug of silica and then extracted with ethyl acetate (4×). The organics combined, washed with brine, dried over Na2SO4, filtered and evaporated to dryness to yield a crude mixture that was purified by column chromatography using a gradient of ethyl acetate in hexanes (0-40%) to give 2-fluoro-N-(2-methoxy-4-pyridyl)-4-(1,1,2,2,2-pentafluoroethyl)benzamide (200 mg, 22%) as an off white solid. ESI-MS m/z calc. 364.06, found 365.3 (M+1)+; Retention time: 1.39 minutes (3 minutes run). 1H NMR (400 MHz, DMSO-d6) δ 10.98 (s, 1H), 8.11 (d, J=6.3 Hz, 1H), 7.95 (dd, J=7.4 Hz, 1H), 7.89 (d, J=9.9 Hz, 1H), 7.72 (d, J=9.1 Hz, 1H), 7.23-7.19 (m, 2H), 3.85 (s, 3H) ppm.

Workup

  1. customwas sealed
  2. filtrationfiltered through a plug of silica
  3. extractionextracted with ethyl acetate (4×)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customto yield a crude mixture that
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-79ab828eb88642f2bf0ea0d0d999198b
Source dataset
uspto-grants-2015_10
Patent number
US09163042B2

Reaction notes

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