Potassium Iodide → 8-Benzyl-2-(furan-2-ylmethyl)-6-phenyl-3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)imidazo[1,2-a]pyrazine

HRID 1627731Notes

Reaction equation

HRID 1627731 reaction equation
N1C=CN2C=CN=CC=12.[CH2:10]([C:17]1[NH:22][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:20][N:19]2[C:29](=[O:38])[C:30]([CH2:32][C:33]3[O:34][CH:35]=[CH:36][CH:37]=3)=[N:31][C:18]=12)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Br[CH2:40][C:41]1[CH:46]=[CH:45][C:44]([B:47]2[O:51][C:50]([CH3:53])([CH3:52])[C:49]([CH3:55])([CH3:54])[O:48]2)=[CH:43][CH:42]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>>[CH2:10]([C:17]1[C:18]2[N:19]([C:29]([O:38][CH2:40][C:41]3[CH:42]=[CH:43][C:44]([B:47]4[O:48][C:49]([CH3:55])([CH3:54])[C:50]([CH3:53])([CH3:52])[O:51]4)=[CH:45][CH:46]=3)=[C:30]([CH2:32][C:33]3[O:34][CH:35]=[CH:36][CH:37]=3)[N:31]=2)[CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:22]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2771670Imidazo(1,2-a)pyrazineHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 1785156418-benzyl-2-(furan-2-ylmethyl)-6-phenyl-7H-imidazo[1,2-a]pyrazin-3-one

Product 1

HCID 712569648-Benzyl-2-(furan-2-ylmethyl)-6-phenyl-3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)imidazo[1,2-a]pyrazineYield 49%

Procedure

Synthesis of 8-benzyl-2-(furan-2-ylmethyl)-6-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)imidazo[1,2-a]pyrazine (4759). To a solution of 8-benzyl-2-(furan-2-ylmethyl)-6-phenylimidazo[1,2-a]pyrazin-3(7H)-one (50 mg, 0.13 mmol) was added 2-(4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (47 mg, 0.16 mmol), potassium carbonate (27 mg, 0.20 mmol) and potassium iodide (33 mg, 0.20 mmol). The reaction mixture was stirred at room temperature for 1 h and heat to 40° C. until HPLC shows the completion of the reaction. After cooling down, the reaction mixture was extracted with ethyl acetate/water. The organic layer was collected and dried over magnesium sulfate. After evaporation, the residue was purified with flash chromatography to give the product as yellow solid (30 mg, 49%). 1H NMR (300 MHz, CD2Cl2, δ): 7.79-7.23 (m, 18H), 7.32 (d, J=6.0 Hz, 2H), 5.11 (s, 2H), 4.53 (s, 2H), 4.15 (s, 2H), 1.53 (s, 12H); MS (ESI) m/z 597.41.

Workup

  1. temperatureheat to 40° C. until HPLC
  2. customthe completion of the reaction
  3. temperatureAfter cooling down
  4. extractionthe reaction mixture was extracted with ethyl acetate/water
  5. customThe organic layer was collected
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporation
  8. customthe residue was purified with flash chromatography

Sources & evidence

ORD record
ord-41ba3dee02474dc9a81dc9357206e204
Source dataset
uspto-grants-2014_07
Patent number
US08785652B2

Reaction notes

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