Cesium carbonate → HCID 58961606, compound

HRID 916967Notes

Reaction equation

HRID 916967 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[C:9]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:27][C:28]1[CH:29]=[C:30]([OH:35])[CH:31]=[CH:32][C:33]=1[F:34].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[C:10]1[C:9]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([O:35][C:30]2[CH:31]=[CH:32][C:33]([F:34])=[C:28]([F:27])[CH:29]=2)[N:11]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 759273,4-DifluorophenolHCID 10309849HCID 10309849, compound

Product 1

HCID 58961606HCID 58961606, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To an oven-dried round bottom flask was added toluene (1 mL), the product of Example 112 (0.050 g; 0.122 mmol), and 3,4-difluorophenol (0.016 g; 0.122 mmol), and cesium carbonate (0.044 g; 0.134 mmol). The reaction mixture was heated at 100° C. and stirred for 4 hours. The reaction mixture was allowed to cool to room temperature, then it was partitioned between ethyl acetate and 2N aq. NaOH solution. The organic portion was separated and washed with more 2N aq. NaOH solution (2×), brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification was done by MPLC (silica gel; 0-10% ethyl acetate:hexane) to afford the desired product: m/e=504 (M+1) Rt=4.61 min on LCMS.

Workup

  1. temperatureto cool to room temperature
  2. customit was partitioned between ethyl acetate and 2N aq. NaOH solution
  3. customThe organic portion was separated
  4. washwashed with more 2N aq. NaOH solution (2×), brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification

Sources & evidence

ORD record
ord-ce7aa0ed951d4995b73af212c91270bd
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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