Sodium Iodide → 6-Iodo-3-phenyl-2,4-bis(trifluoromethyl)quinoline

HRID 627478Notes

Reaction equation

HRID 627478 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:5]2[C:22]([F:25])([F:24])[F:23].CNCCNC.CC(O)(C)C.[Na+].[I-:38]>C(Cl)Cl.[Cu]I>[I:38][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:5]2[C:22]([F:25])([F:24])[F:23]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6386tert-ButanolHCID 8070N,N'-DimethylethylenediamineHCID 867160666-Bromo-3-phenyl-2,4-bis(trifluoromethyl)quinoline2×

Product 1

HCID 867160676-Iodo-3-phenyl-2,4-bis(trifluoromethyl)quinoline

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-bromo-3-phenyl-2,4-bis(trifluoromethyl)quinoline (273 mg, 0.650 mmol, Intermediate 8, step c), CuI (14 mg, 0.074 mmol), N,N′-dimethylethylenediamine (0.0158 mL, 0.147 mmol), t-BuOH (0.65 mL), and NaI (200 mg, 1.33 mmol) was microwaved at 150° C. for 30 min (Biotage). The reaction was diluted with DCM (10 mL), filtered through Celite® and a 0.45 um filter, and concentrated. The residue was flash chromatographed with a heptane to 20% EtOAc/heptane gradient to afford the title compound as a light yellow oil that crystallized upon standing.

Workup

  1. customwas microwaved at 150° C. for 30 min (Biotage)
  2. filtrationfiltered through Celite®
  3. filtrationa 0.45 um filter
  4. concentrationconcentrated
  5. customchromatographed with a heptane to 20% EtOAc/heptane gradient

Sources & evidence

ORD record
ord-516b9288e7df4314937b432741b2beff
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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