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

HRID 1262195Notes

Reaction equation

HRID 1262195 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](B(O)O)=[CH:30][CH:29]=[CH:28][N:27]=1>>[F:25][C:26]1[C:31]([C:2]2[N:10]3[C:5]([CH:6]=[N:7][C:8]([NH:11][C:12]4[CH:13]=[CH:14][C:15]([N:18]5[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]5)=[CH:16][CH:17]=4)=[N:9]3)=[CH:4][CH:3]=2)=[CH:30][CH:29]=[CH:28][N:27]=1

Participants

3

Reactant 2

HCID 27832702-Fluoropyridine-3-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 66712765[7-(2-Fluoro-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

Procedure

[7-(2-Fluoro-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-pyridineboronic acid in an analogous manner to Example 1031b. Product isolated as a yellow solid (78 mg, 68%). m.p.=201-203° C.; LCMS (m/e) 404 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.95-8.87 (m, 1H), 8.74 (s, 1H), 8.23-8.17 (m, 1H), 7.47 (d, 2H, J=7.7 Hz), 7.34-7.27 (m, 1H), 7.19-7.12 (m, 1H), 6.92 (d, 2H, J=8.0 Hz), 6.85 (d, 1H, J=4.7 Hz), 6.68 (s, 1H), 3.23-3.15 (m, 4H), 2.64-2.56 (m, 4H), 2.37 (s, 3H).

Sources & evidence

ORD record
ord-3884c66eca4841ef83b639fad505d31c
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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