1,2-Dimethoxyethane → Ethyl 2-(2-((tert-butoxycarbonyl)(cyclopropylmethyl)amino)pyridin-4-yl)oxazole-4-carboxylate

HRID 632814Notes

Reaction equation

[CH:1]1([CH2:4][N:5]([C:13]2[CH:18]=[C:17](B3OC(C)(C)C(C)(C)O3)[CH:16]=[CH:15][N:14]=2)[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:3][CH2:2]1.Br[C:29]1[O:30][CH:31]=[C:32]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[N:33]=1.C(=O)([O-])[O-].[K+].[K+].COCCOC>O>[C:8]([O:7][C:6]([N:5]([CH2:4][CH:1]1[CH2:2][CH2:3]1)[C:13]1[CH:18]=[C:17]([C:29]2[O:30][CH:31]=[C:32]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[N:33]=2)[CH:16]=[CH:15][N:14]=1)=[O:12])([CH3:9])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butyl (cyclopropylmethyl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate (48.3 g), ethyl 2-bromo-1,3-oxazole-4-carboxylate (25.8 g), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane complex (4.79 g), potassium carbonate (32.4 g) and DME (489 mL)/water (98 mL) was stirred at 80° C. for 4 hr, and poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (33.3 g).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-2811331ff5644e378f6095945fc4d42e
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321757B2

Reaction notes

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