Ethyl Acetate → HCID 58206216, compound

HRID 2067918Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:18]3[C:13](=[C:14]([F:20])[CH:15]=[CH:16][C:17]=3[F:19])[C:12](=[O:21])[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:10]2)=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:35]2[CH:36]=[N:37][N:38](C(OC(C)(C)C)=O)[CH:39]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C1COCC1.C(P([Pd]P(C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C)(C)C.O>[F:20][C:14]1[CH:15]=[CH:16][C:17]([F:19])=[C:18]2[C:13]=1[C:12](=[O:21])[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:10][N:9]2[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([C:35]2[CH:36]=[N:37][NH:38][CH:39]=2)=[CH:7][N:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethyl 1-[(5-bromopyridin-2-yl)methyl]-5,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (3.00 g, 7.09 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (5.42 g, 18.4 mmol), and 1 N cesium carbonate (14.2 mL, 14.2 mmol) in 50 mL of THF under nitrogen was added bis(tri-tert-butylphosphoranyl)palladium (10 mol %). The reaction mixture was heated to 100° C. for 20 hours, then cooled to room temperature. Ethyl acetate (100 mL) and water (100 mL) were added, and the resultant brown solid was collected to provide ethyl 5,8-difluoro-4-oxo-1-{[5-(1H-pyrazol-4-yl)pyridin-2-yl]methyl}-1,4-dihydroquinoline-3-carboxylate that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 411.0 for M+H+.

Workup

temperaturecooled to room temperature
customthe resultant brown solid was collected

Sources & evidence

ORD record: ord-d138d451690b412ba96a850638e4d9ef
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293914B2

Reaction notes

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