Cesium carbonate → HCID 19010514, compound

HRID 1741752Notes

Reaction equation

HRID 1741752 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:9]=[CH:8]1.[C:16]([CH:20]([C:36]1[CH:41]=[CH:40][C:39]2[O:42][CH2:43][O:44][C:38]=2[CH:37]=1)[O:21][C:22]1[C:29]([CH2:30][CH2:31][CH3:32])=[CH:28][C:25]([CH2:26]Br)=[CH:24][C:23]=1[CH2:33][CH2:34][CH3:35])([O:18][CH3:19])=[O:17]>CN(C=O)C>[C:16]([CH:20]([C:36]1[CH:41]=[CH:40][C:39]2[O:42][CH2:43][O:44][C:38]=2[CH:37]=1)[O:21][C:22]1[C:29]([CH2:30][CH2:31][CH3:32])=[CH:28][C:25]([CH2:26][N:9]2[C:10]3[CH:11]=[N:12][CH:13]=[CH:14][C:15]=3[N:7]=[CH:8]2)=[CH:24][C:23]=1[CH2:33][CH2:34][CH3:35])([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 20081759HCID 20081759, compoundHCID 178419860HCID 178419860, compound

Product 1

HCID 19010514HCID 19010514, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Cesium carbonate (156 mg, 0.48 mmol) was added to imidazo[4,5-c]pyridine (28.6 mg, 0.24 mmol) in DMF (3 mL) at room temperature under nitrogen. After stirring for 15 min, a solution of 4-(1-carbomethoxy-1-(3,4-methylenedioxyphenyl)-methoxy)-3,5-dipropylbenzyl bromide (121 mg, 0.26 mmol) in DMF (3 mL) was added and the mixture stirred at 50° C. for 18 h. The mixture was poured onto ice/water and extracted with ethyl acetate (3×30 mL). The combined organic phase was washed with water, brine, dried (magnesium sulfate) and the solvent removed in vacuo. The crude material was purified by flash column chromatography (0 to 5% methanol/methylene chloride) to afford the less polar isomer of the titled compound (19 mg).

Workup

  1. stirringthe mixture stirred at 50° C. for 18 h
  2. additionThe mixture was poured onto ice/water
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. washThe combined organic phase was washed with water, brine
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent removed in vacuo
  7. customThe crude material was purified by flash column chromatography (0 to 5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-2cfd818b6007431d82214af4046f92fa
Source dataset
uspto-grants-1994_08
Patent number
US05334598

Reaction notes

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