Cesium carbonate → HCID 19010488, compound

HRID 1741749Notes

Reaction equation

HRID 1741749 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[C:13]2[N:14]=[CH:15][NH:16][C:12]=2[CH:11]=[CH:10][N:9]=1.[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:14]2[C:13]3[C:8]([Cl:7])=[N:9][CH:10]=[CH:11][C:12]=3[N:16]=[CH:15]2)=[CH:25][C:24]=1[CH2:34][CH2:35][CH3:36])([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 53733644-Chloro-1H-imidazo[4,5-c]pyridineHCID 20081759HCID 20081759, compound

Product 1

HCID 19010488HCID 19010488, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Cesium carbonate (117.3 mg, 0.36 mmol) was added to 4-chloroimidazo[4,5-c]pyridine (25 mg, 0.18 mmol) in DMF (2 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 (106.5 mg, 0.23 mmol) in DMF (2 mL) was added and the mixture stirred at room temperature for 12 h. The mixture was poured onto ice/water and the crude product that precipitated was collected by filtration. The crude material was pre-adsorbed on silica gel and chromatographed (0 to 50% hexane/ethyl acetate) to afford the title compound (25 mg).

Workup

  1. stirringthe mixture stirred at room temperature for 12 h
  2. additionThe mixture was poured onto ice/water
  3. customthe crude product that precipitated
  4. filtrationwas collected by filtration
  5. customchromatographed (0 to 50% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b77aed12fcb1413987d360b69530ac76
Source dataset
uspto-grants-1994_08
Patent number
US05334598

Reaction notes

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