Bromomethyl 3-methoxyphenyl ketone → 8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-a]pyrazine

HRID 2102486Notes

Reaction equation

HRID 2102486 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14](=O)[CH2:15]Br>O1CCOCC1>[Cl:8][C:7]1[C:2]2[N:3]([CH:15]=[C:14]([C:13]3[CH:18]=[CH:19][CH:20]=[C:11]([O:10][CH3:9])[CH:12]=3)[N:1]=2)[CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 2762242-Amino-3-chloropyrazine

Product 1

HCID 578031348-Chloro-2-(3-methoxyphenyl)imidazo[1,2-a]pyrazineYield 19.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-3-chloropyrazine (0.20 g, 1.5 mmol, 1.00 equiv) and 3-methoxyphenacyl bromide (0.71 g, 3.1 mmol, 2.0 equiv) in dioxane (10 mL) was heated at 90° C. for 3 hr. The resulting mixture was cooled to rt and filtered. The filtrate was partitioned between 10% IPA/DCM and 1 N NaOH. The aqueous extract was washed with 10% IPA/DCM (2×) and the combined organic extracts were washed with brine and dried with sodium sulfate. Concentration afforded 8-chloro-2-(3-methoxy-phenyl)-imidazo[1,2-a]pyrazine (76 mg, 19%). MH+ (LCMS) 260.1 (m/z).

Workup

  1. filtrationfiltered
  2. customThe filtrate was partitioned between 10% IPA/DCM and 1 N NaOH
  3. extractionThe aqueous extract
  4. washwas washed with 10% IPA/DCM (2×)
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried with sodium sulfate
  7. concentrationConcentration

Sources & evidence

ORD record
ord-1c1f3453b9fd493eb3f7ad0d8d0f7853
Source dataset
uspto-grants-2009_08
Patent number
US07576085B2

Reaction notes

Loading…