[3-(Hydroxymethyl)phenyl]boronic acid → HCID 66712385, compound

HRID 1262436Notes

Reaction equation

HRID 1262436 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][CH:15]=[C:14]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[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:14]2[CH:13]=[C:12]([NH:11][C:8]3[N:7]=[CH:6][C:5]4=[CH:4][CH:3]=[C:2]([C:31]5[CH:32]=[C:27]([CH2:26][OH:25])[CH:28]=[CH:29][CH:30]=5)[N:10]4[N:9]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 66711673HCID 66711673, compound

Product 1

HCID 66712385HCID 66712385, compoundYield 20%

Procedure

Analogous to Example 1504, (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine (0.0731 g, 0.189 mmol) and (3-Hydroxymethylphenyl)boronic acid (0.0513 g, 0.338 mmol) were reacted to afford (3-{2-[3-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-phenyl)-methanol as a yellow powder (15 mg, 20%). LCMS: 415 (M+H); 1H-NMR (CDCl3): 8.70 (s, 1H), 8.21 (s, 1H), 7.92 (s, 1H), 7.62 (d, 1H, J=6.96 Hz), 7.49 (m, 2H), 7.20 (t, 1H, J=8.19 Hz), 6.93 (d, 1H, J=4.50 Hz), 6.88 (s, 1H), 6.84 (d, 1H, J=4.50 Hz), 6.87 (d, 1H, J=8.19 Hz), 4.77 (s, 2H), 2.98 (t, 4H, J=4.96 Hz), 2.44 (t, 4H, J=4.96 Hz), 2.34 (s, 3H).

Sources & evidence

ORD record
ord-d5dde63e089e4a24bd40b8e4920a3ee6
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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