Iodopyrazine → HCID 86730393, compound

HRID 871132Notes

Reaction equation

HRID 871132 reaction equation
I[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.C([Mg]Cl)CCC.[Br:14][C:15]1[C:16]([F:23])=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19]>C1COCC1.C(Cl)Cl>[Br:14][C:15]1[C:16]([F:23])=[C:17]([CH:18]([C:2]2[CH:7]=[N:6][CH:5]=[CH:4][N:3]=2)[OH:19])[CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 642841IodopyrazineHCID 220193613-Bromo-2-fluorobenzaldehydeHCID 178418265HCID 178418265, compound

Product 1

HCID 86730393HCID 86730393, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2-iodopyrazine (0.195 mL, 1.970 mmol) in THF (3.28 mL) at 0° C. was slowly added butyl magnesium chloride (0.985 mL, 1.970 mmol). The mixture was allowed to stir for 30 min, then 3-bromo-2-fluorobenzaldehyde (0.400 g, 1.970 mmol) was added. After 2 hr, the reaction was quenched with a saturated aqueous solution of NH4Cl. The reaction mixture was diluted with CH2Cl2. The layers were separated. The aqueous phase was extracted with CH2Cl2 (2×). The organic phases were combined, dried over Na2SO4, filtered, and concentrated to afford a yellow residue. The crude material was dissolved in a minimal amount of CH2Cl2 to be chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (40 g column, 40 mL/min, 30-70% EtOAc in hexanes over 19 min, tr=12 min) gave the title compound (347 mg, 1.226 mmol, 62.2% yield) as a yellow residue.

Workup

  1. customat 0° C.
  2. waitAfter 2 hr
  3. customthe reaction was quenched with a saturated aqueous solution of NH4Cl
  4. additionThe reaction mixture was diluted with CH2Cl2
  5. customThe layers were separated
  6. extractionThe aqueous phase was extracted with CH2Cl2 (2×)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford a yellow residue
  11. customto be chromatographed
  12. customPurification of the crude material by silica gel chromatography
  13. customan ISCO machine (40 g column, 40 mL/min, 30-70% EtOAc in hexanes over 19 min, tr=12 min)

Sources & evidence

ORD record
ord-a55af1f5e495458986421505abc9a19b
Source dataset
uspto-grants-2015_03
Patent number
US08969586B2

Reaction notes

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