Cesium carbonate → HCID 71150135, compound

HRID 1466234Notes

Reaction equation

Br[C:2]1[CH:19]=[CH:18][C:5]([CH2:6][NH:7][C:8](=[O:17])[C:9]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:16])=[CH:4][C:3]=1[CH3:20].[O:21]=[C:22]1[CH:27]=[C:26](B(O)O)[CH:25]=[CH:24][NH:23]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Cl:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([Cl:15])[C:9]=1[C:8]([NH:7][CH2:6][C:5]1[CH:18]=[CH:19][C:2]([C:26]2[CH:25]=[CH:24][NH:23][C:22](=[O:21])[CH:27]=2)=[C:3]([CH3:20])[CH:4]=1)=[O:17]

Participants

Conditions

Temperature: 85 °C

Procedure

N-(4-Bromo-3-methylbenzyl)-2,6-dichlorobenzamide (0.13 g, 0.35 mmol), 2-oxo-1,2-dihydropyridin-4-ylboronic acid (0.053 g, 0.39 mmol), cesium carbonate (0.34 g, 1.05 mmol), [1,1′Bis(diphenylphosphino(ferrocene]dichloropalladium(II) (25 mg, 0.035 mmol) were dissolved in degassed DMF (3 mL) and H2O (1.5 mL). The reaction mixture was degassed again by bubbling nitrogen through for 15 min then heated in the microwave at 85° C. for 20 min The reaction mixture was diluted with EtOAc and extracted three times with water. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuum. The resulting solid was purified by reverse phase chromatography to afford 2,6-dichloro-N-(3-methyl-4-(2-oxo-1,2-dihydropyridin-4-yl)benzyl)benzamide.

Workup

customThe reaction mixture was degassed again
customby bubbling nitrogen through for 15 min
additionwas diluted with EtOAc
extractionextracted three times with water
dry with materialThe organic phase was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuum
customThe resulting solid was purified by reverse phase chromatography

Sources & evidence

ORD record: ord-92a4f769f7f24cb585ee3d45d8e0a049
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000015B2

Reaction notes

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