Cesium carbonate → HCID 57625502, compound

HRID 2390451Notes

Reaction equation

HRID 2390451 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=4)=[CH:12][C:11]3=[O:26])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:31][C@H:32]1[O:34][CH2:33]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[O:34]1[CH2:33][C@H:32]1[CH2:31][N:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=4)=[CH:12][C:11]3=[O:26])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoateHCID 576255401-(1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one

Product 1

HCID 57625502HCID 57625502, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 1-(1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (1.1 g, 3.1 mmol), (S)-(+)-glycidyl nosylate (0.96 g, 3.7 mmol) and cesium carbonate (1.5 g, 4.6 mmol) in methyl sulfoxide (10 mL) was stirred at ambient temperature overnight. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure. Purification by column chromatography (silica gel, ethyl acetate) gave the title compound (510 mg, 40%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 8.08 (s, 1H), 7.76-7.73 (m, 5H), 7.64 (d, J=9.0 Hz, 1H), 7.51 (d, J=7.0 Hz, 1H), 7.47 (dd, J=9.0, 2.0 Hz, 1H), 6.92 (d, J=2.0 Hz, 1H), 6.52 (dd, J=7.5, 2.0 Hz, 1H), 4.78 (dd, J=15.5, 3.5 Hz, 1H), 4.48 (dd, J=15.0, 5.5 Hz, 1H), 3.41-3.38 (m, 1H), 2.88 (app t, J=4.5 Hz, 1H), 2.60 (dd, J=5.0, 3.0 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organic extracts were washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-80ea1c78d7444e16b26a3668717c554d
Source dataset
uspto-grants-2012_09
Patent number
US08273770B2

Reaction notes

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