[3-(Hydroxymethyl)phenyl]boronic acid → (3-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-phenyl)-methanol

HRID 1262403Notes

Reaction equation

HRID 1262403 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.[OH:25][CH2:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1>>[CH3:24][N:21]1[CH2:22][CH2:23][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:29]5[CH:28]=[C:27]([CH2:26][OH:25])[CH:32]=[CH:31][CH:30]=5)[N:10]4[N:9]=3)=[CH:17][CH:16]=2)[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 2734662[3-(Hydroxymethyl)phenyl]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 66711788(3-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-phenyl)-methanolYield 81.5%

Procedure

Analogous to Example 1497, (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (0.125 g, 0.323 mmol) and (3-Hydroxymethylphenyl)-boronic acid (98.1 mg, 0.646 mmol) were reacted to afford (3-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-phenyl)-methanol (109 mg; Yield=81.5%). LCMS (HPLC): 0.74 min, m/z=415 (M+H); 1H-NMR (DMSO-d6): 9.22 (s, 1H), 8.93 (s, 1H), 8.19 (s, 1H), 7.99 (d, 1H, J=7.8 Hz), 7.64 (d, 2H, J=9.0 Hz), 7.49 (m, 1H), 7.37 (d, 1H, J=7.6 Hz), 7.13 (d, 1H, J=4.7 Hz), 6.92 (m, 3H), 5.25 (t, 1H, J=5.8 Hz), 4.60 (d, 2H, J=5.8 Hz), 3.08 (m, 4H), 2.46 (m, 4H), 2.23 (s, 3H).

Sources & evidence

ORD record
ord-5987518d2ea447d186015b8c87f04e08
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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