Sodium Carbonate → methyl 2-(2-methyl-1H-indol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate

HRID 1403458Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[C:6](B1OC(C)(C)C(C)(C)O1)[CH:5]=2.Cl[C:21]1[C:30]([N:31]2[CH2:35][CH2:34][CH2:33][C@@H:32]2[CH3:36])=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:37]([O:39][CH3:40])=[O:38])[CH:27]=2)[N:22]=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>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:21]1[C:30]([N:31]3[CH2:35][CH2:34][CH2:33][C@@H:32]3[CH3:36])=[N:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:37]([O:39][CH3:40])=[O:38])[CH:27]=3)[N:22]=1)=[CH:6][CH:5]=2

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-methyl-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (378 mg, 1.47 mmol) in ethylene glycol dimethyl ether (5.5 mL) and water (3 drops) was added methyl 2-chloro-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate (150 mg, 0.49 mmol), sodium carbonate (156 mg, 1.47 mmol) and Pd(PPh3)4 (29 mg, 0.03 mmol) with stirring for 2 h at 90° C. in an oil bath under an inert atmosphere of nitrogen. The reaction mixture was concentrated under reduced pressure to give the residue, which was purified by silica gel column chromatography (2% ethyl acetate in petroleum ether) to afford methyl 2-(2-methyl-1H-indol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate as light yellow solid (140 mg, 71%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customto give the residue, which
customwas purified by silica gel column chromatography (2% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-e82767cb461a4cc7a6e2134edd6ee125
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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