2-Fluoropyridine-3-boronic acid → HCID 58204391, compound

HRID 1629255Notes

Reaction equation

HRID 1629255 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13]([C:15]4[N:19]([CH2:20][C:21]([F:24])([F:23])[F:22])[N:18]=[CH:17][N:16]=4)[N:14]=[C:7]3[C:6]=2[CH:25]=1.[F:26][C:27]1[C:32](B(O)O)=[CH:31][CH:30]=[CH:29][N:28]=1>>[F:26][C:27]1[C:32]([C:2]2[CH:3]=[CH:4][C:5]3[O:11][CH2:10][CH2:9][N:8]4[CH:12]=[C:13]([C:15]5[N:19]([CH2:20][C:21]([F:22])([F:23])[F:24])[N:18]=[CH:17][N:16]=5)[N:14]=[C:7]4[C:6]=3[CH:25]=2)=[CH:31][CH:30]=[CH:29][N:28]=1

Participants

3

Reactant 2

HCID 27832702-Fluoropyridine-3-boronic acidHCID 58204561HCID 58204561, compound

Product 1

HCID 58204391HCID 58204391, compoundYield 55%

Procedure

Following the procedure for 203, 10-bromo-2-(1-(2,2,2-trifluoroethyl)-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine was reacted with 2-fluoropyridin-3-ylboronic acid to give 10-(2-fluoropyridin-3-yl)-2-(1-(2,2,2-trifluoroethyl)-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (0.108 g, 55%), 1H NMR (400 MHz, DMSO) δ 8.71 (t, J=2.0, 1H), 8.57-7.83 (m, 4H), 7.80-7.39 (m, 2H), 7.22 (d, J=8.5, 1H), 5.88 (q, J=8.8, 2H), 4.79-4.38 (m, 4H). MS (ESI(+)): m/z 431.1 (M+H), which was hydrolyzed with HCl to give 218 (0.072 g, 72%). 1H NMR (400 MHz, DMSO) δ 11.85 (s, 1H), 8.78 (d, J=2.3, 1H), 8.09 (d, J=2.8, 2H), 7.69 (ddd, J=8.9, 7.7, 2.2, 2H), 7.36 (t, J=23.8, 1H), 7.08 (d, J=8.6, 1H), 6.30 (t, J=6.7, 1H), 5.91 (q, J=8.8, 2H), 4.56 (dd, J=13.5, 5.5, 4H). MS (ESI(+)): m/z 429.1 (M+H)

Sources & evidence

ORD record
ord-2ca8da37b28d4aa285d5624f383af72f
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

Loading…