2-Fluoro-6-methylpyridine-3-boronic acid → 4-Amino-8-(2-fluoro-6-methylpyridin-3-yl)-cinnoline-3-carboxylic acid propylamide
Reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14].[F:19][C:20]1[C:25](B(O)O)=[CH:24][CH:23]=[C:22]([CH3:29])[N:21]=1>>[CH2:16]([NH:15][C:13]([C:3]1[N:4]=[N:5][C:6]2[C:11]([C:2]=1[NH2:1])=[CH:10][CH:9]=[CH:8][C:7]=2[C:25]1[C:20]([F:19])=[N:21][C:22]([CH3:29])=[CH:23][CH:24]=1)=[O:14])[CH2:17][CH3:18]Participants
3
Procedure
The title compound was prepared from 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (300.0 mg, 0.97 mmol) and 2-fluoro-6-methylpyridine-3-boronic acid (426.7 mg, 2.75 mmol) according to Method A to afford a white solid (124.2 mg, 38%). 1H NMR (300.132 MHz, CDCl3) δ 8.53 (bs, 1H), 7.94 (t, J=1.4 Hz, 1H), 7.92 (dt, J=8.6, 1.4 Hz, 1H), 7.89 (d, J=7.6 Hz, 1H), 7.83 (dt, J=7.1, 1.2 Hz, 1H), 7.74 (dd, J=8.8, 7.3 Hz, 1H), 7.19 (dd, J=7.4, 1.3 Hz, 1H), 3.46 (q, J=6.7 Hz, 2H), 2.59 (s, 3H), 1.66 (sextet, J=7.3 Hz, 2H), 1.00 (t, J=7.4 Hz, 3H). MS APCI, m/z=340 (M+H). HPLC 2.28 min.
Sources & evidence
- ORD record
- ord-b4928274bfa64023814c8ee70b1acc47
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07465795B2
Reaction notes
Loading…