Sodium Carbonate → HCID 89793899, compound

HRID 1056308Notes

Reaction equation

HRID 1056308 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.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.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>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[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

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 21226129Dichloromethane methanolHCID 897835202-(3-chloro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89793899HCID 89793899, compoundYield 91.5%

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; 36.7 mg, 0.117 mmol), (2-fluorophenyl)boronic acid (CombiBlocks, Inc., San Diego, Calif.; 24.63 mg, 0.176 mmol), Na2CO3 (37.3 mg, 0.352 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 6.78 mg, 5.87 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-(2-fluorophenyl)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (39.8 mg, 0.107 mmol, 91% yield) as a brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 12.07 (1H, br. s.), 8.10 (1H, dd, J=7.4, 1.2 Hz), 7.90 (1H, dd, J=8.2, 1.2 Hz), 7.78 (1H, t, J=8.0 Hz), 7.50-7.62 (2H, m), 7.38 (1H, td, J=7.5, 1.0 Hz), 7.27-7.34 (1H, m), 7.25 (1H, br. s.), 5.39 (1H, br. s.), 3.61 (2H, td, J=6.8, 2.0 Hz), 2.89 (2H, t, J=6.9 Hz), 2.75 (3H, d, J=1.6 Hz). 19F NMR (377 MHz, CDCl3) δ ppm −114.59 (1F, br. s.). m/z (ESI, +ve) 373.0 (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-381c0b6352a44839b9982aeea4afe58d
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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