Water → HCID 24739304, compound

HRID 731657Notes

Reaction equation

HRID 731657 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[C:12]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[N:13][O:14][C:15]=3[CH3:16])[N:10]=2)[CH:7]=1.[C:23]([NH2:31])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.Cl.C(OCC)(=O)C.[Cu]I>[CH3:16][C:15]1[O:14][N:13]=[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]=1[C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([NH:31][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:7][N:6]2[CH:8]=1

Participants

9

Reactant 4

HCID 962WaterHCID 2331Benzamide2×HCID 10796Cesium carbonateHCID 24738994HCID 24738994, compound

Product 1

HCID 24739304HCID 24739304, compoundYield 12.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A microwave tube containing 6-iodo-2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridine (100 mg, 0.25 mmol), benzamide (30 mg, 0.25 mmol) and cesium carbonate (162 mg, 0.5 mmol) in DMF (1.2 mL) was evacuated and then back-filled with Ar several time and then sealed. The resulting mixture was heated to 150° C. in the microwave for 3 h and then additional benzamide (30 mg, 0.25 mmol) and CuI (5 mg, 0.025 mmol) added and the resulting mixture heated to 200° C. in the microwave (2×30 min). The resulting mixture was then poured into water and extracted with ethyl acetate. The combined organic layers were then washed with brine, dried over sodium sulphate and evaporated to leave a brown gum. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 25:75) afforded a solid that was then diluted with hydrochloric acid (1 N) and ethyl acetate. The precipitate was filtered off to afford the title compound (12.1 mg, 12%) which was obtained as a light yellow solid. MS: m/e=395.0 [M+H]+.

Workup

  1. customwas evacuated
  2. additionback-filled with Ar several time
  3. customsealed
  4. temperaturethe resulting mixture heated to 200° C. in the microwave (2×30 min)
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were then washed with brine
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. customto leave a brown gum
  10. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 25:75)
  11. customafforded a solid
  12. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-3f250452a6414214a7244f689b473cd0
Source dataset
uspto-grants-2009_09
Patent number
US07585874B2

Reaction notes

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