(6-Fluoro-5-methylpyridin-3-yl)boronic acid → [7-(6-Fluoro-5-methyl-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

HRID 1262200Notes

Reaction equation

HRID 1262200 reaction equation
Br[C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)=[CH:14][CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[F:25][C:26]1[C:31]([CH3:32])=[CH:30][C:29](B(O)O)=[CH:28][N:27]=1>>[F:25][C:26]1[N:27]=[CH:28][C:29]([C:2]2[N:10]3[C:5]([CH:6]=[N:7][C:8]([NH:11][C:12]4[CH:17]=[CH:16][C:15]([N:18]5[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]5)=[CH:14][CH:13]=4)=[N:9]3)=[CH:4][CH:3]=2)=[CH:30][C:31]=1[CH3:32]

Participants

3

Reactant 2

HCID 17750247(6-Fluoro-5-methylpyridin-3-yl)boronic acidHCID 66711200(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

Product 1

HCID 66711923[7-(6-Fluoro-5-methyl-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

Procedure

[7-(6-Fluoro-5-methyl-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine was prepared from (7-bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine and 2-fluoro-3-methylpyridine-5-boronic acid in an analogous manner to Example 1031b. Product isolated as a yellow solid (66 mg, 56%). m.p.=210° C.; LCMS (m/e) 418 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.71 (s, 1H), 8.61-8.53 (m, 2H), 7.52-7.45 (m, 2H), 6.99-6.92 (m, 3H), 6.82 (d, 1H, J=4.8 Hz), 6.66 (bs, 1H), 3.22-3.16 (m, 4H), 2.63-2.57 (m, 4H), 2.37 (s, 3H), 2.37 (s, 3H).

Sources & evidence

ORD record
ord-509b14d33325411596e4b7c61d060f08
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…