1-(2,5-Difluorobenzyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine → 5-[1-(2,5-Difluorobenzyl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl]-nicotinic acid ethyl ester
Reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13](I)=[CH:14][C:6]1=2.[CH2:21]([O:23][C:24](=[O:39])[C:25]1[CH:30]=[C:29](B2OC(C)(C)C(C)O2)[CH:28]=[N:27][CH:26]=1)[CH3:22]>>[CH2:21]([O:23][C:24](=[O:39])[C:25]1[CH:30]=[C:29]([C:13]2[CH:12]=[N:11][C:7]3[NH:8][CH2:9][CH2:10][N:5]([CH2:4][C:3]4[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:2]=4[F:1])[C:6]=3[CH:14]=2)[CH:28]=[N:27][CH:26]=1)[CH3:22]Participants
3
Reactant 2
Product 1
Procedure
1-(2,5-Difluorobenzyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (350 mg) was reacted with 5-(4,4,5-trimethyl-[1,3,2]dioxaborolan-2-yl)-nicotinic acid ethyl ester as in General Procedure 4A to give the title compound as a tan solid (29% yield). M.p. 169-172° C., LCMS: m/z=411.03 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.42 (t, J=7.1 Hz, 3H), 3.47-3.52 (m, 2H), 3.62-3.71 (m, 2H), 4.42 (q, J=7.1 Hz, 2H), 4.51 (s, 2H), 4.99 (s, 1H), 6.75 (s, 1H), 6.91-7.02 (m, 2H), 7.03-7.11 (m, 1H), 7.74 (d, J=2.0 Hz, 1H), 8.28 (d, J=2.3 Hz, 1H), 8.79 (d, J=2.3 Hz, 1H), 9.08 (d, J=2.0 Hz, 1H).
Sources & evidence
- ORD record
- ord-aa79bafe262e40d8822c59a601a41639
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08080561B2
Reaction notes
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