Potassium Phosphate, Tribasic → Ethyl 3-amino-6-cyclopropylpicolinate

HRID 1260290Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8](Br)[N:7]=1)=[O:5])[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P([CH:35]2[CH2:40][CH2:39]CCC2)C2CCCCC2)CCCCC1.C1(B(O)O)CC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([CH:39]2[CH2:40][CH2:35]2)[N:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-amino-6-bromo-pyridine-2-carboxylic acid ethyl ester (prepared according to US 2006/199960; 1.0 g, 4.08 mmol), potassium phosphate (3.03 g, 14.3 mmol), tricyclohexylphosphine (0.228 g, 0.82 mmol) and water (1.25 ml) in toluene (25 ml) was added cyclopropylboronic acid (0.91 g, 10.6 mmol) and palladium (II) acetate (90 mg, 0.4 mmol). The resulting suspension was stirred at 100° C. for 24 hours. After solvent evaporation, the title compound was obtained after silica gel chromatography using a heptane/ethyl acetate gradient as yellow solid (0.374 g, 44%).

Workup

customAfter solvent evaporation

Sources & evidence

ORD record: ord-aeb34e84ee0a43df8afcd9a8a3513f44
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470820B2

Reaction notes

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