Sodium Carbonate → HCID 178497320, compound

HRID 1403313Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[C:10]([C:14]([F:17])([F:16])[F:15])=[N:11][NH:12][CH:13]=2)O1.Cl[C:20]1[C:29]([N:30]([CH:32]([CH3:34])[CH3:33])[CH3:31])=[N:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:35]([O:37][CH3:38])=[O:36])[CH:26]=2)[N:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:32]([N:30]([CH3:31])[C:29]1[C:20]([C:9]2[C:10]([C:14]([F:15])([F:16])[F:17])=[N:11][NH:12][CH:13]=2)=[N:21][C:22]2[C:27]([N:28]=1)=[CH:26][C:25]([C:35]([O:37][CH3:38])=[O:36])=[CH:24][CH:23]=2)([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (536.0 mg, 2.05 mmol) in DME (5 mL) and water (0.5 mL) was added methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (200.0 mg, 0.68 mmol), sodium carbonate (217.0 mg, 2.05 mmol) and Pd(PPh3)4 (39 mg, 0.03 mmol) with stirring for 0.5 h at 90° C. in an oil bath with an inert atmosphere of nitrogen. The reaction mixture was concentrated under vacuum to get a residue, which was purified by a silica gel column with 2%-10% ethyl acetate in petroleum to afford methyl 3-(isopropyl(methyl)amino)-2-(3-(trifluoromethyl)-1H-pyrazol-4-yl)quinoxaline-6-carboxylate as a light yellow solid (80 mg, 30%).

Workup

concentrationThe reaction mixture was concentrated under vacuum
customto get a residue, which
customwas purified by a silica gel column with 2%-10% ethyl acetate in petroleum

Sources & evidence

ORD record: ord-f3fdd1a814f84057b9579ec823508770
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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