Iodine → HCID 57704778, compound

HRID 2093214Notes

Reaction equation

HRID 2093214 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13](N)=[C:12]([CH3:17])[CH:11]=1.N(OCCC(C)C)=O.[I:26]I>C(Cl)(Cl)Cl>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([C:10]2[CH:15]=[CH:14][C:13]([I:26])=[C:12]([CH3:17])[CH:11]=2)=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 8053Isoamyl NitriteHCID 54912447HCID 54912447, compound

Product 1

HCID 57704778HCID 57704778, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2′-fluoro-4′-methoxy-3-methylbiphenyl-4-amine (190 mg, 0.822 mmol), 3-methylbutyl nitrite (144.4 mg, 1.233 mmol), iodine (251 mg, 0.986 mmol) and chloroform (7 ml) were refluxed in an oil bath for 3.5 hours then allowed to cooled to ambient overnight. Reaction crude was purified by flash chromatography (SiO2, Biotage 40+M cartridge) eluted with a EtOAc/hexanes gradient mixture. Related fractions were pooled and concentrated in vacuo to afford the title compound. LCMS was showing the solid to be about 70A % pure. LCMS (ESI) calc.=LCMS (ESI) calc.=341.99; found=341.94 (M)+.

Workup

  1. temperatureto cooled to ambient overnight
  2. customReaction crude
  3. customwas purified by flash chromatography (SiO2, Biotage 40+M cartridge)
  4. washeluted with a EtOAc/hexanes gradient mixture
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dfe8e856254140b5a46371732218bee6
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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