Cesium carbonate → HCID 86637364, compound

HRID 1040368Notes

Reaction equation

HRID 1040368 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2[N:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][C:17]=2OS(C(F)(F)F)(=O)=O)[CH:12]=[CH:13][C:14]=1[Cl:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34](=[N:47][NH2:48])([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CCOCC.O.Cl[Pd]Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2[N:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][C:17]=2[NH:48][N:47]=[C:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:12]=[CH:13][C:14]=1[Cl:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 79304DiphenylmethylidenehydrazineHCID 86637361HCID 86637361, compound

Product 1

HCID 86637364HCID 86637364, compoundYield 88.5%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 1140TolueneSolventHCID 21584184Diethylether waterSolvent

Conditions

Temperature
90 °C

Procedure

Put 2 g (4 mmol) of methyl 6-[3-(benzyloxy)-4-chlorophenyl]-5-{[(trifluoromethyl)sulphonyl]oxy}pyridine-2-carboxylate in 10 mL of anhydrous toluene in a screw-top bottle. To the solution, under argon, add successively 938 mg (4.78 mmol) of benzophenone hydrazone, 1.95 g (6 mmol) of caesium carbonate and 65 mg (0.08 mmol) of PdCl2 (dppf). Heat the reaction mixture for 3 h at 90° C. while stirring, then distribute in 100 mL of ether/water 1:1 mixture. Dry the organic phase over Na2SO4 and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluting with a DCM/acetone gradient from 0 to 5% of acetone. After concentration under reduced pressure, we obtain 1.94 g of methyl 6-[3-(benzyloxy)-4-chlorophenyl]-5-[2-(diphenylmethylidene)hydrazino]pyridine-2-carboxylate in the form of oil.

Workup

  1. dry with materialDry the organic phase over Na2SO4
  2. concentrationconcentrate under reduced pressure
  3. customPurify the residue
  4. customobtained by silica gel column chromatography
  5. washeluting with a DCM/acetone gradient from 0 to 5% of acetone
  6. concentrationAfter concentration under reduced pressure, we

Sources & evidence

ORD record
ord-25e0b6dd61af4ac4b6f535fdb52b92ed
Source dataset
uspto-grants-2013_10
Patent number
US08552201B2

Reaction notes

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