Potassium Carbonate → HCID 46913422, compound

HRID 1025389Notes

Reaction equation

HRID 1025389 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:12]=[N:13][C:14]([O:19][CH3:20])=[C:15]([O:17][CH3:18])[CH:16]=3)=[CH:9][N:10]=2)[CH:7]=1.[O:21]1[CH2:25][CH2:24][NH:23][C:22]1=[O:26].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.O1CCOCC1>[CH3:18][O:17][C:15]1[CH:16]=[C:11]([C:8]2[N:6]3[CH:7]=[C:2]([N:23]4[CH2:24][CH2:25][O:21][C:22]4=[O:26])[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)[CH:12]=[N:13][C:14]=1[O:19][CH3:20]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 739492-OxazolidinoneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 46913420HCID 46913420, compound

Product 1

HCID 46913422HCID 46913422, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a 5 mL microwave tube was added 6-bromo-3-(5,6-dimethoxypyridin-3-yl)imidazo[1,2-a]pyridine (0.070 g, 0.21 mmol), 2-oxazolidinone (0.027 g, 0.31 mmol), copper(I) iodide (4.0 mg, 0.021 mmol), (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (0.0033 ml, 0.021 mmol), potassium carbonate (0.025 ml, 0.42 mmol), and dioxane (3 mL). The resulting reaction mixture was sealed and heated to 100° C. in closed system for 6 h. The mixture was cooled to rt and the solvent was removed. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, 12 g SiO2, methylene chloride:methanol=94%:6%, Flow=30 mL/min). A peak at 15 min was collected. The solvent was removed in vacuo to afford the desired product as white solid (20 mg). MS (ESI pos. ion) m/z: 341.0. Calcd exact mass for C14H12BrN3O2: 340.12. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.87 (s, 3H) 3.94 (s, 3H) 4.12 (t, J=7.89 Hz, 2H) 4.46 (t, J=7.89 Hz, 2H) 7.57 (s, 1H) 7.63 (d, J=1.61 Hz, 1H) 7.69-7.75 (m, 1H) 7.79 (s, 1H) 7.98 (s, 1H) 8.72 (s, 1H).

Workup

  1. customThe resulting reaction mixture
  2. customwas sealed
  3. temperatureThe mixture was cooled to rt
  4. customthe solvent was removed
  5. customThe crude product was purified
  6. customA peak at 15 min was collected
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b4f951c3604e4d98956f9e46e9d21b9e
Source dataset
uspto-grants-2014_05
Patent number
US08729074B2

Reaction notes

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