Methyl Acrylate → HCID 70655482, compound

HRID 1472504Notes

Reaction equation

HRID 1472504 reaction equation
[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)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:22]([O:26][CH3:27])(=[O:25])[CH:23]=[CH2:24]>[Cu]I.O1CCCC1.CCN(CC)CC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11](/[CH:24]=[CH:23]/[C:22]([O:26][CH3:27])=[O:25])=[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

Participants

5

Reactant 2

HCID 7294Methyl AcrylateHCID 86670200HCID 86670200, compound

Product 1

HCID 70655482HCID 70655482, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 68616177Triethylamine tetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,3-bis(4-fluorophenyl)-5-iodopyrazine (400 mg, 1.02 mmol, 1.00 equiv), methyl acrylate (1.8 g, 20.93 mmol, 20.62 equiv), CuI (193 mg, 1.02 mmol, 1.00 equiv), Pd(PPh3)Cl2 (285 mg, 0.41 mmol, 0.40 equiv), and tetrahydrofuran/Et3N (2/1 mL) was stirred overnight at 80° 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 120 mg (28%) of (E)-methyl 3-(5,6-bis(4-fluorophenyl)pyrazin-2-yl)acrylate as a grey solid.

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 120 mg (28%) of (E)-methyl 3-(5,6-bis(4-fluorophenyl)pyrazin-2-yl)acrylate as a grey solid

Sources & evidence

ORD record
ord-63e690d52fd940aa9e9c126fafee5e84
Source dataset
uspto-grants-2015_04
Patent number
US09012637B2

Reaction notes

Loading…