Cesium carbonate → HCID 18461153, compound

HRID 2303377Notes

Reaction equation

HRID 2303377 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([F:29])[CH:23]=2)=[O:21])=[CH:5][CH:4]=1.Cl.Cl[CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[C:24]([F:29])[CH:23]=2)=[O:21])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 18461160HCID 18461160, compound

Product 1

HCID 18461153HCID 18461153, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

900 mg (2.20 mmol) of [2-(4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][3-fluoro-4-hydroxyphenyl]methanone was dissolved in 12 mL of DMF and 810 mg (4.4 mmol) of 1-(2-chloroethyl)piperidine hydrochloride was added. To the reaction mixture was added 3.3 g (10 mmol) of Cs2CO3 and heated to reflux for one hour. The reaction mixture was filtered to remove the solids. The solvents were removed by evaporation and the residue was chromatographed on a silica gel column eluted with a linear gradient of beginning with CHCl3 and ending with MeOH-CHCl3 (1:19). The desired fractions were determined by tlc, combined, and evaporated to a solid. This yielded 960 mg of the title compound as a tan amorphous solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for one hour
  3. filtrationThe reaction mixture was filtered
  4. customto remove the solids
  5. customThe solvents were removed by evaporation
  6. customthe residue was chromatographed on a silica gel column
  7. washeluted with a linear gradient
  8. customevaporated to a solid

Sources & evidence

ORD record
ord-a7da850993e54d3aaff6e1ec926a15a0
Source dataset
uspto-grants-2002_08
Patent number
US06432982B1

Reaction notes

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