Cesium carbonate → HCID 90416411, compound

HRID 633589Notes

Reaction equation

HRID 633589 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9](F)=[C:10]([C:12]2[C:20]3[C:15](=[C:16]([O:26][CH3:27])[N:17]=[C:18]([C:21]#[C:22][CH2:23][CH2:24][OH:25])[CH:19]=3)[N:14]([CH3:28])[CH:13]=2)[CH:11]=1)(=[O:5])=[O:4])[CH3:2].[F:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[OH:38].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[F:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[O:38][C:9]1[CH:8]=[CH:7][C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:11][C:10]=1[C:12]1[C:20]2[C:15](=[C:16]([O:26][CH3:27])[N:17]=[C:18]([C:21]#[C:22][CH2:23][CH2:24][OH:25])[CH:19]=2)[N:14]([CH3:28])[CH:13]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 90417779HCID 90417779, compound

Product 1

HCID 90416411HCID 90416411, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of Example 126B (50 mg, 0.120 mmol), 2,4-difluorophenol (15.62 mg, 0.120 mmol) and cesium carbonate (58.7 mg, 0.180 mmol) in dimethylsulfoxide (0.5 mL) was heated at 120° C. in a microwave oven (Biotage Smith Synthesizer) for 45 minutes. The reaction mixture was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate (3×). The combined organic phases were washed with water (2×), saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated and the residue was absorbed on silica gel and purified by flash chromatography (silica gel, 20-90% ethyl acetate/heptanes) to give the title compound (38 mg, 60% yield)

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×)
  3. washThe combined organic phases were washed with water (2×), saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was absorbed on silica gel
  8. custompurified by flash chromatography (silica gel, 20-90% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-b627ae1fc6f0483ba2d80230ed4eafc5
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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