Potassium Iodide → HCID 86722757, compound

HRID 587777Notes

Reaction equation

HRID 587777 reaction equation
[I-:1].[K+].CN[C@@H]1CCCC[C@H]1NC.Br[C:14]1[CH:22]=[C:21](/[CH:23]=[CH:24]/[CH:25]([C:30]2[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=2)[C:26]([F:29])([F:28])[F:27])[CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]>O1CCOCC1.[Cu]I>[I:1][C:14]1[CH:22]=[C:21](/[CH:23]=[CH:24]/[CH:25]([C:30]2[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=2)[C:26]([F:29])([F:28])[F:27])[CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 86722549(E)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzoic acid

Product 1

HCID 86722757HCID 86722757, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Per Buchwald, et al.; JACS, 2002, 124, 14844-14845, potassium iodide (KI, 273 mg, 1.64 mmol), CuI (31 mg, 0.16 mmol) and trans-N,N′-dimethylcyclohexane-1,2-diamine (catalytic amount) were added to a solution of (E)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzoic acid (400 mg, 0.82 mmol) in 1,4-dioxane (8 mL). The mixture in an Ace pressure tube was heated at 100° C. for 3 h. The reaction mixture was brought to ambient temperature and filtered through a Celite® pad. The filtrate was concentrated and residue was diluted with EtOAc and washed with 1N HCl followed by brine. The organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography on silica eluting with 25% EtOAc in petroleum ether to afford the title compound as brown semi solid (240 mg, 55%): 1H NMR (400 MHz, DMSO-d6) δ 13.3 (bs, 1H), 8.21 (s, 1H), 7.91 (s, 2H), 7.71-7.64 (m, 2H), 7.01 (dd, J=15.6, 9.2 Hz, 1H), 6.75 (d, J=15.6 Hz, 1H), 4.85-4.81 (m, 1H); ESIMS m/z 532.8 ([M−H]−); IR (thinfilm) 3436, 1699, 1113, 750 cm−1.

Workup

  1. customwas brought to ambient temperature
  2. filtrationfiltered through a Celite® pad
  3. concentrationThe filtrate was concentrated
  4. additionresidue was diluted with EtOAc
  5. washwashed with 1N HCl
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica eluting with 25% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-a61bd96ff1fb47c4b135d7a5a818c9b6
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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