Cesium carbonate → 6-(3-Chloro-phenyl)-5-cyclopropyl-pyridine-2-carboxylic acid methyl ester

HRID 927429Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH2:12]2)=[C:7](Br)[N:6]=1)=[O:4].[Cl:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(Cl)Cl.[Pd](Cl)Cl.O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH2:12]2)=[C:7]([C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:15])[CH:21]=2)[N:6]=1)=[O:4]

Participants

Conditions

Temperature: 110 °C

Procedure

6-Bromo-5-cyclopropyl-pyridine-2-carboxylic acid methyl ester (0.1 g, 0.4 mmol), 3-chlorophenylboronic acid (CAN 63503-60-6, 0.08 g, 0.5 mmol), 1,1′-bis(diphenylphosphino)-ferrocene-palladium(II)dichloride methylene chloride adduct (CAN 95464-05-4, 50 mg) and cesium carbonate (CAN 534-17-8, 0.2 g, 0.6 mmol) was added into 1,4-dioxane (10 mL) under nitrogen atmosphere. The mixture was stirred for 12 h at 110° C. Subsequently, the mixture was concentrated to give crude product. The crude product was purified by a flash column chromatography (silica gel, 5 g, 20% ethyl acetate in petroleum ether) to give product (80 mg, 71%); MS: (EI) m/e 288.1 [M+H]+.

Workup

concentrationSubsequently, the mixture was concentrated
customto give crude product
customThe crude product was purified by a flash column chromatography (silica gel, 5 g, 20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-cb92640b67e443148af5591fe61562bd
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290451B2

Reaction notes

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