4-Methylpyridine-3-Boronic Acid → [4-(4-Methyl-piperazin-1-yl)-phenyl]-[7-(4-methyl-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

HRID 1262193Notes

Reaction equation

HRID 1262193 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.[CH3:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][C:27]=1B(O)O>>[CH3:24][N:21]1[CH2:20][CH2:19][N:18]([C:15]2[CH:14]=[CH:13][C:12]([NH:11][C:8]3[N:7]=[CH:6][C:5]4=[CH:4][CH:3]=[C:2]([C:27]5[CH:28]=[N:29][CH:30]=[CH:31][C:26]=5[CH3:25])[N:10]4[N:9]=3)=[CH:17][CH:16]=2)[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 27627114-Methylpyridine-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 66712528[4-(4-Methyl-piperazin-1-yl)-phenyl]-[7-(4-methyl-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

Procedure

[4-(4-Methyl-piperazin-1-yl)-phenyl]-[7-(4-methyl-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-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 4-methylpyridine-3-boronic acid in an analogous manner to Example 1031b. Product isolated as a yellow foam (28 mg, 25%). LCMS (m/e) 400 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.75-8.69 (m, 2H), 8.58-8.52 (m, 1H), 7.35 (d, 2H, J=7.5 Hz), 7.31-7.25 (m, 1H), 6.88-6.79 (m, 3H), 6.79-6.74 (m, 1H), 6.65 (s, 1H), 3.17-3.10 (m, 4H), 2.61-2.54 (m, 4H), 2.35 (s, 3H), 2.30 (s, 3H).

Sources & evidence

ORD record
ord-47534a4f95514f81877cada9cc4a8609
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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