7-iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one → 1-[1-(2-Chloro-3,6-difluorophenyl)ethyl]-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one
Reaction equation
[I:1][C:2]1[CH:12]=[N:11][C:5]2[NH:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.Br[CH:14]([C:16]1[C:21]([Cl:22])=[C:20]([F:23])[CH:19]=[CH:18][C:17]=1[F:24])[CH3:15]>>[Cl:22][C:21]1[C:20]([F:23])=[CH:19][CH:18]=[C:17]([F:24])[C:16]=1[CH:14]([N:9]1[C:8](=[O:10])[CH2:7][NH:6][C:5]2[N:11]=[CH:12][C:2]([I:1])=[CH:3][C:4]1=2)[CH3:15]Participants
3
Procedure
7-Iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (2.935 g) was treated with 2-(1-bromoethyl)-3-chloro-1,4-difluorobenzene (Preparation 3) as in General Procedure 1 to give the title compound as an orange solid (11% yield). LCMS: m/z=449.86 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 1.79 (3H, m), 2.73 (1H, s), 2.89 (1H, s), 5.76 (1H, m), 6.96 (1H, s), 7.29 (1H, m), 7.43 (1H, m), 7.62 (1H, s), 7.83 (1H, m).
Sources & evidence
- ORD record
- ord-2528a147c4e3428f9455fe4ed1b9bc2f
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07919502B2
Reaction notes
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