Sodium Carbonate → 2-(2-methyl-3-(2-methylfuran-3-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

HRID 1056313Notes

Reaction equation

HRID 1056313 reaction equation
Cl[C:2]1[C:3]([CH3:22])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2.CC1(C)C(C)(C)OB([C:31]2[CH:35]=[CH:34][O:33][C:32]=2[CH3:36])O1.C([O-])([O-])=O.[Na+].[Na+].CO.C(Cl)Cl>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>[CH3:22][C:3]1[C:2]([C:31]2[CH:35]=[CH:34][O:33][C:32]=2[CH3:36])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:12]2[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=2)[N:4]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 21226129Dichloromethane methanolHCID 242295474,4,5,5-Tetramethyl-2-(2-methylfuran-3-yl)-1,3,2-dioxaborolaneHCID 89783520HCID 89783520, compound

Product 1

HCID 897937312-(2-methyl-3-(2-methylfuran-3-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-oneYield 84%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-(3-chloro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 425; 36.5 mg, 0.117 mmol), 4,4,5,5-tetramethyl-2-(2-methylfuran-3-yl)-1,3,2-dioxaborolane (Maybridge, Tintagel, UK; 0.040 mL, 0.175 mmol), Na2CO3 (37.1 mg, 0.350 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 6.74 mg, 5.84 μmol) in a mixture of 1,4-dioxane (1.5 mL) and water (0.500 mL) was stirred under argon at 100° C. for 20 min. The reaction mixture was then concentrated onto silica gel and chromatographically purified (silica gel, 50-100% EtOAc/hexanes, then 0-10% MeOH/DCM) to provide 2-(2-methyl-3-(2-methylfuran-3-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (35.1 mg, 0.098 mmol, 84% yield) as a yellow-orange solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.79 (1H, br. s.), 8.03 (1H, dd, J=7.3, 1.5 Hz), 7.83 (1H, dd, J=8.2, 1.2 Hz), 7.78 (1H, d, J=7.4 Hz), 7.74 (1H, d, J=2.0 Hz), 7.30 (1H, d, J=2.2 Hz), 7.00 (2H, d, J=1.8 Hz), 3.41 (2H, td, J=6.8, 2.4 Hz), 2.88 (2H, t, J=6.8 Hz), 2.75 (3H, s), 2.48 (3H, s). m/z (ESI, +ve) 359.0 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated onto silica gel
  2. customchromatographically purified (silica gel, 50-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-dfab02096df5440285313027a3bde1d4
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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