1-Methyl-2-(tributylstannyl)-1H-imidazole → HCID 89793846, compound

HRID 1056312Notes

Reaction equation

HRID 1056312 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.[CH3:23][N:24]1[CH:28]=[CH:27][N:26]=[C:25]1[Sn](CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1.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:25]2[N:24]([CH3:23])[CH:28]=[CH:27][N:26]=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

5

Reactant 2

HCID 27632521-Methyl-2-(tributylstannyl)-1H-imidazoleHCID 89783520HCID 89783520, compound

Product 1

HCID 89793846HCID 89793846, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

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; 34.1 mg, 0.109 mmol), 1-methyl-2-(tributylstannyl)-1H-imidazole (Indofine Chemical Company, Inc.; 0.042 mL, 0.131 mmol) and Pd(PPh3)4 (Strem Chemicals, Inc.; 12.60 mg, 10.90 μmol) in toluene (2.0 mL) was stirred under argon at 110° C. for 1 h. The reaction mixture was then cooled to RT and diluted with hexanes (10 mL). The precipitated solid was collected by vacuum filtration (fine glass frit), sequentially washed with hexanes (10 mL) and Et2O (10 mL), and dried in vacuo to provide 2-(2-methyl-3-(1-methyl-1H-imidazol-2-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (34.7 mg, 0.097 mmol, 89% yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.70 (1H, br. s.), 7.97 (1H, dd, J=7.1, 1.3 Hz), 7.91 (1H, s), 7.85 (1H, dd, J=8.2, 1.2 Hz), 7.75-7.82 (1H, m), 7.66 (1H, d, J=0.6 Hz), 7.07 (1H, d, J=2.0 Hz), 6.98 (1H, br. s.), 3.79 (3H, s), 3.42 (2H, td, J=6.8, 2.2 Hz), 2.88 (2H, br. s.), 2.83-2.86 (3H, m). m/z (ESI, +ve) 359.0 (M+H)+.

Workup

  1. filtrationThe precipitated solid was collected by vacuum filtration (fine glass frit)
  2. washsequentially washed with hexanes (10 mL) and Et2O (10 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-280bf41f9d1f468ab96fcbac099cc5f7
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…