Cesium carbonate → HCID 23108667, compound

HRID 336831Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].FC(F)(F)S(O[C:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(COC)OC.O>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=2)=[CH:5][CH:4]=1)=[O:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To 400 mg (2.67 mmol) of 4-formyl-phenylboronic acid diluted in a dimethoxyethane/water mixture (40 ml/4 ml) are respectively added 1.33 g (5.78 mmol) of tert-butyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate, 154 mg (0.133 mmol) of palladium tetrakistriphenylphosphine and 1.74 g (5.34 mmol) of cesium carbonate. The solution is purged under argon then stirred at 80° C. for 18 h and filtered on Celite with ethyl acetate. The filtrate is washed with water, then with sodium chloride saturated solution, dried over magnesium sulfate, and concentrated. The residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 85:15 to 70:30) to yield 677 mg of tert-butyl 4-(4-formylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate in the form of a yellow oil.

Workup

customThe solution is purged under argon
filtrationfiltered on Celite with ethyl acetate
washThe filtrate is washed with water
dry with materialwith sodium chloride saturated solution, dried over magnesium sulfate
concentrationconcentrated
customThe residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 85:15 to 70:30)

Sources & evidence

ORD record: ord-f92f56a2043e42f1a257e92b61d78fbe
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889711B2

Reaction notes

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