Cesium carbonate → HCID 19010505, compound

HRID 1741746Notes

Reaction equation

HRID 1741746 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][C:8]1[NH:9][C:10]2[C:11]([N:16]=1)=[N:12][CH:13]=[CH:14][CH:15]=2.[C:17]([CH:21]([C:37]1[CH:42]=[CH:41][C:40]2[O:43][CH2:44][O:45][C:39]=2[CH:38]=1)[O:22][C:23]1[C:30]([CH2:31][CH2:32][CH3:33])=[CH:29][C:26]([CH2:27]Br)=[CH:25][C:24]=1[CH2:34][CH2:35][CH3:36])([O:19][CH3:20])=[O:18]>CN(C=O)C>[C:17]([CH:21]([C:37]1[CH:42]=[CH:41][C:40]2[O:43][CH2:44][O:45][C:39]=2[CH:38]=1)[O:22][C:23]1[C:30]([CH2:31][CH2:32][CH3:33])=[CH:29][C:26]([CH2:27][N:16]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[CH3:7])=[CH:25][C:24]=1[CH2:34][CH2:35][CH3:36])([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 34910692-METHYL-1H-IMIDAZO[4,5-B]PYRIDINEHCID 20081759HCID 20081759, compound

Product 1

HCID 19010505HCID 19010505, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

Cesium carbonate (294 mg, 0.902 mmol) was added to 2-methylimidazo[4,5-b]pyridine (60 mg, 0.451 mmol) in DMF (2 mL) at room temperature under nitrogen. After stirring at 50° C. for 15 min, a solution of 4-(1-carbomethoxy-1-(3,4-methylenedioxyphenyl)methoxy)-3,5-dipropylbenzyl bromide (from Step C) (27 1 mg, 0.585 mmol) in DMF (2 mL) was added and the mixture stirred at 50° C. for 12 h. After cooling to room temperature, the mixture was poured onto ice/water and extracted with ethyl acetate (4 times). The combined organic phase was washed with water twice, brine, dried (magnesium sulfate) and the solvent removed in vacuo. The crude product (a mixture of regioisomers) was purified by flash chromatography on silica-gel (3,4,5% methanol/methylene chloride) to provide the title compound (87 mg).

Workup

  1. stirringthe mixture stirred at 50° C. for 12 h
  2. temperatureAfter cooling to room temperature
  3. additionthe mixture was poured onto ice/water
  4. extractionextracted with ethyl acetate (4 times)
  5. washThe combined organic phase was washed with water twice
  6. dry with materialbrine, dried (magnesium sulfate)
  7. customthe solvent removed in vacuo
  8. additionThe crude product (a mixture of regioisomers)
  9. customwas purified by flash chromatography on silica-gel (3,4,5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-9b01ad571b004d82ac559a02318c665b
Source dataset
uspto-grants-1994_08
Patent number
US05334598

Reaction notes

Loading…