Iodine → HCID 86670200, compound

HRID 1472503Notes

Reaction equation

HRID 1472503 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11](N)=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[I:22]I.N(OCCC(C)C)=O>[Cu]I.COCCOC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:12][C:11]([I:22])=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 807IodineHCID 8053Isoamyl NitriteHCID 70654521HCID 70654521, compound

Product 1

HCID 86670200HCID 86670200, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 5,6-bis(4-fluorophenyl)pyrazin-2-amine (1 g, 3.53 mmol, 1.00 equiv), ethylene glycol dimethyl ether (50 mL), I2 (450 mg, 1.78 mmol, 0.50 equiv), CuI (200 mg, 1.05 mmol, 0.30 equiv), and isoamyl nitrite (2.75 g, 10.87 mmol, 3.08 equiv) was stirred for 10 min at room temperature, then for an additional 2 h at 60° C. in an oil bath. The resulting mixture was concentrated in vacuo, and purified via silica gel column chromatography (ethyl acetate/petroleum ether (1:40)) resulting in 1 g (72%) of 2,3-bis(4-fluorophenyl)-5-iodopyrazine as brown oil.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. custompurified via silica gel column chromatography (ethyl acetate/petroleum ether (1:40))
  3. customresulting in 1 g (72%) of 2,3-bis(4-fluorophenyl)-5-iodopyrazine as brown oil

Sources & evidence

ORD record
ord-0f0dd16e37274ca2b4b7291d287e2312
Source dataset
uspto-grants-2015_04
Patent number
US09012637B2

Reaction notes

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