Potassium Phosphate, Tribasic → HCID 86664351, compound

HRID 1909028Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][N:7]=[C:6](Br)[CH:5]=1.[CH3:12][N:13]1[C:17]([CH3:18])=[C:16](B2OC(C)(C)C(C)(C)O2)[C:15]([CH3:28])=[N:14]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[C:16]1[C:15]([CH3:28])=[N:14][N:13]([CH3:12])[C:17]=1[CH3:18]

Participants

Conditions

Temperature: 80 °C

Procedure

To a microwave reactor tube was added 2-bromo-isonicotinic acid methyl ester (150 mg, 0.69 mmol), 1,3,5-trimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (197 mg, 0.83 mmol) and Pd2(PtBu3)2(14 mg, 0.028 mmol) and 1,4-dioxane (2 mL). The mixture was degassed and then 2M aqueous K3PO4 (0.46 mL, 1.4 mmol) was added. The mixture was heated in a microwave reactor at 80° C. for 1 hour. The cooled mixture was partitioned between CHCl3 and water. The organic layer was isolated and the product purified by SiO2 chromatography (0-15% MeOH in EtOAc) to give 2-(1,3,5-trimethyl-1H-pyrazol-4-yl-isonicotinic acid methyl ester (68 mg, 21%) as a yellow gum. MS(ESI) m/z 246 [M+H]+.

Workup

customThe mixture was degassed
customThe cooled mixture was partitioned between CHCl3 and water
customThe organic layer was isolated
customthe product purified by SiO2 chromatography (0-15% MeOH in EtOAc)

Sources & evidence

ORD record: ord-175dae6747994a59bb391bc6cf790331
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598217B2

Reaction notes

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