N-Methylaniline → 2-(3-(methyl(phenyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one
Reaction equation
F[C:2]1[CH:3]=[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.[CH3:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>>[CH3:22][N:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]1[CH:3]=[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]=2Participants
Conditions
- Temperature
- 0 °C
Procedure
Prepared similarly to that described in Example 210 using 2-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 210i; 56 mg, 0.198 mmol), N-methylaniline (150 μl, 1.389 mmol, Alfa Aesar, Ward Hill, Mass.), and NaHMDS (1.0M in THF; 1389 μl, 1.389 mmol) and heating at 0° C. for 1 h. Purification by silica gel (100% DCM to 3% MeOH/DCM) provided 2-(3-(methyl(phenyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (46% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.76 (t, J=6.94 Hz, 2H) 3.33 (s, 3H) 3.42 (td, J=6.80, 2.45 Hz, 2H) 6.97 (br. s., 1H) 7.15 (d, J=2.15 Hz, 1H) 7.41-7.49 (m, 2H) 7.50-7.55 (m, 2H) 7.56-7.62 (m, 2H) 7.70 (dd, J=8.02, 1.17 Hz, 1H) 8.01 (dd, J=7.53, 1.27 Hz, 1H) 8.45 (s, 1H) 11.70 (br. s., 1H). MS (ESI, pos. ion) m/z: 370.2 (M+1).
Workup
- customPrepared similarly to that
- customPurification by silica gel (100% DCM to 3% MeOH/DCM)
Sources & evidence
- ORD record
- ord-8886ece685904c65a354fc2098ebd34f
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394297B2
Reaction notes
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