2-Isopropoxypyridine-3-boronic acid → 5-{2-Fluoro-4-[2-(1-methylethoxy)pyridin-3-yl]phenyl}pyrazin-2-amine

HRID 1523923Notes

Reaction equation

HRID 1523923 reaction equation
[CH:1]([O:4][C:5]1[C:10](B(O)O)=[CH:9][CH:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].Br[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:22]=[CH:23][C:24]([NH2:27])=[N:25][CH:26]=2)=[C:17]([F:28])[CH:16]=1>>[F:28][C:17]1[CH:16]=[C:15]([C:10]2[C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:20]=[CH:19][C:18]=1[C:21]1[N:22]=[CH:23][C:24]([NH2:27])=[N:25][CH:26]=1

Participants

3

Reactant 2

HCID 467393182-Isopropoxypyridine-3-boronic acidHCID 903128885-(4-Bromo-2-fluorophenyl)pyrazin-2-amine

Product 1

HCID 903135555-{2-Fluoro-4-[2-(1-methylethoxy)pyridin-3-yl]phenyl}pyrazin-2-amine

Procedure

The title compound was prepared using methods analogous to those described in Example 369 using (2-isopropoxypyridin-3-yl)boronic acid and 5-(4-bromo-2-fluorophenyl)pyrazin-2-amine in Step B. MS (ESI): mass calcd. for C18H17FN4O, 324.14; m/z found, 325.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.63-8.57 (m, 1H), 8.18-8.13 (m, 1H), 8.12 (d, J=1.4, 1H), 7.99-7.90 (m, 1H), 7.69-7.62 (m, 1H), 7.58-7.41 (m, 2H), 6.98-6.91 (m, 1H), 5.49-5.35 (m, 1H), 4.68 (s, 2H), 1.37 (d, J=6.2, 6H).

Sources & evidence

ORD record
ord-b1d58261c49c482e9da97d54b6ec0285
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

Loading…