Ethyl Acetate → HCID 70664668, compound

HRID 1403346Notes

Reaction equation

[O:1]1[C:10]2[C:5](=[CH:6][C:7](B3OC(C)(C)C(C)(C)O3)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Cl[C:21]1[C:30]([N:31]([CH:33]([CH3:35])[CH3:34])[CH3:32])=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:36]([O:38][CH3:39])=[O:37])[CH:27]=2)[N:22]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(OCC)(=O)C>O1CCOCC1.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>[O:1]1[C:10]2[C:5](=[CH:6][C:7]([C:21]3[C:30]([N:31]([CH:33]([CH3:35])[CH3:34])[CH3:32])=[N:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([C:36]([O:38][CH3:39])=[O:37])[CH:27]=4)[N:22]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of 2-(chroman-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (320 mg, 1.23 mmol) in dioxane (5.0 mL) was added methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (Scheme I, 180 mg, 0.61 mmol), K3PO4 (392 mg, 1.86 mmol), Pd(PPh3)4 (35.8 mg, 0.03 mmol) and water (3 drops) with stirring for 4 h at 95° C. maintained with an inert atmosphere of nitrogen in an oil bath. The reaction mixture was concentrated under vacuum to give the residue, which was applied onto a silica gel column with 2% ethyl acetate in petroleum ether to afford methyl 2-(chroman-6-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate as a light yellow solid (130 mg, 51%).

Workup

temperaturemaintained with an inert atmosphere of nitrogen in an oil bath
concentrationThe reaction mixture was concentrated under vacuum
customto give the residue, which

Sources & evidence

ORD record: ord-bee61f13d4c74abfb56a0091a1e00bf9
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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