(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-morpholin-4-yl-phenyl)-amine

HRID 1262201Notes

Reaction equation

HRID 1262201 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][O:21][CH2:20][CH2:19]4)=[CH:14][CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[F:24][C:25]1[C:30]([CH3:31])=[CH:29][C:28](B(O)O)=[CH:27][N:26]=1>>[F:24][C:25]1[N:26]=[CH:27][C:28]([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][O:21][CH2:22][CH2:23]5)=[CH:14][CH:13]=4)=[N:9]3)=[CH:4][CH:3]=2)=[CH:29][C:30]=1[CH3:31]

Participants

3

Reactant 2

HCID 17750247(6-Fluoro-5-methylpyridin-3-yl)boronic acidHCID 54578326(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-(4-morpholin-4-yl-phenyl)-amine

Product 1

HCID 66711982[7-(6-Fluoro-5-methyl-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-morpholin-4-yl-phenyl)-amine

Procedure

[7-(6-Fluoro-5-methyl-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-morpholin-4-yl-phenyl)-amine was prepared from (7-bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-(4-morpholin-4-yl-phenyl)-amine and 2-fluoro-3-methylpyridine-5-boronic acid in an analogous manner to Example 1031b. Product isolated as a yellow solid (79 mg, 66%). m.p.=227-230° C.; LCMS (m/e) 405 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.71 (s, 1H), 8.62 (s, 1H), 8.56-8.49 (m, 1H), 7.51 (d, 2H, J=8.9 Hz), 6.99-6.90 (m, 3H), 6.83 (d, 1H, J=4.8 Hz), 6.68 (bs, 1H), 3.92-3.85 (m, 4H), 3.17-3.10 (m, 4H), 2.38 (s, 3H).

Sources & evidence

ORD record
ord-795a0981d3f0459196a70ea4eda89815
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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