Potassium Phosphate, Tribasic → HCID 11419860, compound

HRID 269728Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][C:19]([C:21]2[CH:22]=[N:23][C:24](Cl)=[CH:25][CH:26]=2)=[O:20])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8].[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][C:19]([C:21]2[CH:22]=[N:23][C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:25][CH:26]=2)=[O:20])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-chloro-2-(6-chloropyridin-3-yl-carbonylamino)-N-(5-chloropyridin-2-yl)benzamide (Intermediate E-2, 0.42167 g, 1 mmol) in 10 mL of DME was added phenyl boronic acid (0.134 g, 1.1 mmol) and an aqueous solution of potassium phosphate (0.6 mL, 1 molar solution). The reaction mixture was degassed and tetrakistriphenyl-phosphine palladium (60 mg) was added. The mixture was heated at 80° C. overnight, cooled to room temperature, diluted with ethyl acetate (50 mL), washed with water, saturated sodium bicarbonate, and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the crude product was purified by RPHPLC [ethyl acetate/hexane (3:7)]. Yield=0.280 g.

Workup

customThe reaction mixture was degassed
additiontetrakistriphenyl-phosphine palladium (60 mg) was added
temperaturecooled to room temperature
additiondiluted with ethyl acetate (50 mL)
washwashed with water, saturated sodium bicarbonate
dry with materialdried over anhydrous magnesium sulfate
customAfter evaporation of the solvent
customthe crude product was purified by RPHPLC [ethyl acetate/hexane (3:7)]

Sources & evidence

ORD record: ord-63054047505d4eb2a166792ad87c18d9
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449457B2

Reaction notes

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