1,1'-Carbonyldiimidazole → 6-bromo-1-(1H-indol-5-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one

HRID 85033Notes

Reaction equation

HRID 85033 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[C:5]([NH2:18])=[N:4][CH:3]=1.[C:19](N1C=CN=C1)(N1C=CN=C1)=[O:20]>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C:9]3[CH:10]=[C:11]4[C:15](=[CH:16][CH:17]=3)[NH:14][CH:13]=[CH:12]4)[C:19](=[O:20])[NH:18][C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 727136316-bromo-N2-(1H-indol-5-yl)pyrazine-2,3-diamine

Product 1

HCID 727136326-bromo-1-(1H-indol-5-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-oneYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 6-bromo-N2-(1H-indol-5-yl)pyrazine-2,3-diamine (0.450 g, 1.48 mmol) in THF (5 mL) was added carbonyldiimidazole (1.20 g, 7.40 mmol). The resulting mixture was heated at 65° C. for 48 hr, after which it was concentrated in vacuo and partitioned between EtOAc and H2O. The organic layer was separated, dried over MgSO4, filtered, and concentrated in vacuo to yield a residue that was purified via silica gel chromatography eluting with EtOAc to yield the title compound (0.20 g, 41%). HPLC retention time: 2.07 minutes; MS ESI (m/z): 330.2/332.2 (M+1)+, calc. 329.

Workup

  1. concentrationafter which it was concentrated in vacuo
  2. custompartitioned between EtOAc and H2O
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a residue that
  8. customwas purified via silica gel chromatography
  9. washeluting with EtOAc

Sources & evidence

ORD record
ord-753f991557c143769f9c1ecc2827e41f
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

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