Cesium fluoride → HCID 89785053, compound

HRID 1056309Notes

Reaction equation

HRID 1056309 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.C([Sn](CCCC)(CCCC)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)CCC.[F-].[Cs+].CO.C(Cl)Cl>O1CCOCC1.CN(C=O)C.[Cu]I.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:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[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

9

Reactant 4

HCID 25953Cesium fluorideHCID 6077842-(Tributylstannyl)pyridineHCID 21226129Dichloromethane methanolHCID 89783520HCID 89783520, compound

Product 1

HCID 89785053HCID 89785053, compoundYield 72.1%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °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; 38.0 mg, 0.122 mmol), 2-(tributylstannyl)pyridine (Aldrich; 0.043 mL, 0.134 mmol), CuI (2.314 mg, 0.012 mmol), cesium fluoride (36.9 mg, 0.243 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 7.02 mg, 6.08 μmol) in a mixture of 1,4-dioxane (2.0 mL) and DMF (2.0 mL) was stirred in a sealed tube under argon at 140° C. for 1 h. 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-(pyridin-2-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (31.2 mg, 0.088 mmol, 72% yield) as a brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 12.20 (1H, br. s.), 8.85 (1H, d, J=4.5 Hz), 8.09 (1H, dd, J=7.4, 1.0 Hz), 7.94-8.01 (1H, m), 7.90 (2H, d, J=8.2 Hz), 7.74-7.81 (1H, m), 7.50 (1H, ddd, J=7.3, 4.9, 1.1 Hz), 7.25 (1H, br. s.), 5.32 (1H, br. s.), 3.63 (2H, td, J=6.8, 2.1 Hz), 2.97 (3H, s), 2.94 (2H, t, J=6.8 Hz). m/z (ESI, +ve) 356.0 (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-c30cde72cae44283bca87f63f572cac8
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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