Sodium Carbonate → HCID 89793854, compound

HRID 1056311Notes

Reaction equation

HRID 1056311 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.[O:23]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24]1.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>[O:23]1[CH:27]=[CH:26][C:25]([C:2]2[C:3]([CH3:22])=[N:4][C:5]3[C:10]([N:11]=2)=[C:9]([C:12]2[NH:20][C:19]4[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=4[CH:13]=2)[CH:8]=[CH:7][CH:6]=3)=[CH:24]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 21226129Dichloromethane methanolHCID 89783520HCID 89783520, compound

Product 1

HCID 89793854HCID 89793854, compoundYield 89%

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; 37.7 mg, 0.121 mmol), furan-3-ylboronic acid (Boron Molecular, Research Triangle, N.C.; 20.23 mg, 0.181 mmol), Na2CO3 (38.3 mg, 0.362 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 6.96 mg, 6.03 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-(3-(furan-3-yl)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (37.0 mg, 0.107 mmol, 89% yield) as a yellow-orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.81 (1H, br. s.), 8.52 (1H, s), 8.02 (1H, dd, J=7.2, 1.4 Hz), 7.95 (1H, t, J=1.7 Hz), 7.83 (1H, dd, J=8.2, 1.4 Hz), 7.74-7.80 (1H, m), 7.25 (1H, s), 7.24 (1H, dd, J=1.8, 0.8 Hz), 7.00 (1H, br. s.), 3.45 (2H, td, J=6.7, 2.3 Hz), 2.90-2.94 (2H, m), 2.90 (3H, s). m/z (ESI, +ve) 344.9 (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-e2c7e9a806444c8bb2a0cc0a88fa59b8
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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