Sodium Carbonate → HCID 89785208, compound

HRID 1056307Notes

Reaction equation

HRID 1056307 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.[Cl: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>[Cl: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 27343222-Chlorophenylboronic acidHCID 21226129Dichloromethane methanolHCID 89783520HCID 89783520, compound

Product 1

HCID 89785208HCID 89785208, compoundYield 84.6%

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; 38.4 mg, 0.123 mmol), (2-chlorophenyl)boronic acid (Aldrich; 28.8 mg, 0.184 mmol), Na2CO3 (39.0 mg, 0.368 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 7.09 mg, 6.14 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-chlorophenyl)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (40.3 mg, 0.104 mmol, 84% yield) as a brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 12.00 (1H, br. s.), 8.11 (1H, dd, J=7.6, 1.2 Hz), 7.92 (1H, dd, J=8.4, 1.2 Hz), 7.79 (1H, t, J=8.0 Hz), 7.59-7.64 (1H, m), 7.46-7.55 (3H, m), 7.24 (1H, d, J=2.2 Hz), 5.65 (1H, br. s.), 3.61 (2H, t, J=6.7 Hz), 2.89 (2H, td, J=6.7, 1.4 Hz), 2.67 (3H, s). m/z (ESI, +ve) 388.9 (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-d2f147a2ec574a8c9b9b0b21ac85dcde
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…