Potassium Carbonate → Tert-butyl 3-(3-methylpyridin-4-yl)benzoate

HRID 39452

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH3:8].[C:9]([O:13][C:14]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[C:20]1[CH:21]=[C:16]([CH:17]=[CH:18][CH:19]=1)[C:14]([O:13][C:9]([CH3:11])([CH3:12])[CH3:10])=[O:15]

Participants

Conditions

Temperature: 80 °C

Procedure

4-Chloro-3-methylpyridine (2.00 g, 15.7 mmol), 3-(tert-butoxycarbonyl)phenylboronic acid (5.42 g, 24.4 mmol), a 2M aqueous solution of potassium carbonate (31.4 mL, 62.8 mmol), and palladium tetrakis(triphenylphosphine) (Pd(PPh3)4, 0.906 g, 0.784 mmol) were suspended in 1,2-dimethoxyethane (DME, 150 mL). The resulting mixture was stirred and heated to 80° C. for 60 hours. The crude reaction mixture was cooled to room temperature and then the layers were separated. The organic layer was evaporated to dryness and then purified on 120 g of silica gel utilizing a gradient of 0-70% ethyl acetate in hexanes to yield the pure product as a pale yellow oil (3.02 g, 11.2 mmol, 71.4%).

Workup

customThe crude reaction mixture
temperaturewas cooled to room temperature
customthe layers were separated
customThe organic layer was evaporated to dryness
custompurified on 120 g of silica gel utilizing a gradient of 0-70% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-64835593af164625acd46d84ea8a7db0
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524910B2

Linked notes

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