3-Aminophenylboronic acid → HCID 22329549, compound

HRID 586328Notes

Reaction equation

HRID 586328 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:12]1[N:16]2[N:17]=[CH:18][C:19]([C:21]([F:24])([F:23])[F:22])=[N:20][C:15]2=[N:14][CH:13]=1>>[F:24][C:21]([F:22])([F:23])[C:19]1[CH:18]=[N:17][N:16]2[C:12]([C:4]3[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=3)=[CH:13][N:14]=[C:15]2[N:20]=1

Participants

3

Reactant 2

HCID 922693-Aminophenylboronic acidHCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazine

Product 1

HCID 22329549HCID 22329549, compoundYield 41%

Procedure

This reaction was carried out as in Example 6, step b, using a mixture of 3-aminophenylboronic acid (290 mg, 1.87 mmol) and 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (250 mg, 0.93 mmol). The residue was purified by flash chromatography (silica gel, 35% EtOAc/isohexane) to give 105 mg (41%) of the title compound: 1H NMR (400 MHz, CDCl3) δ 3.87 (2H, br s), 6.80 (1H, ddd, J 7.9, 2.4, 0.8 Hz), 7.34 (1H, t, J 7.9 Hz), 7.46-7.43 (2H, m), 8.57 (1H, s), 8.77 (1H, s); MS (ES+) m/z 280 [M+H]+.

Workup

  1. customThe residue was purified by flash chromatography (silica gel, 35% EtOAc/isohexane)

Sources & evidence

ORD record
ord-76338bed81f845769624d36c5f486c67
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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