2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol → 7-(4-Fluoro-2-methoxyphenyl)-α,α-dimethylimidazo[1,2-b][1,2,4]triazine-3-methanol

HRID 891865Notes

Reaction equation

HRID 891865 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[C:4]([O:17][CH3:18])[CH:3]=1.Br[C:20]1[N:24]2[N:25]=[CH:26][C:27]([C:29]([OH:32])([CH3:31])[CH3:30])=[N:28][C:23]2=[N:22][CH:21]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:20]2[N:24]3[N:25]=[CH:26][C:27]([C:29]([OH:32])([CH3:30])[CH3:31])=[N:28][C:23]3=[N:22][CH:21]=2)=[C:4]([O:17][CH3:18])[CH:3]=1

Participants

3

Reactant 2

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 222400914-Fluoro-2-Methoxybenzeneboronic acid pinacol ester, 96%

Product 1

HCID 222400807-(4-Fluoro-2-methoxyphenyl)-α,α-dimethylimidazo[1,2-b][1,2,4]triazine-3-methanolYield 91%

Procedure

2-(4-Fluoro-2-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane was coupled to 2-(7-bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol (from Example 1, step d) under the conditions described in Example 1, step e. The residue was purified by flash column chromatography (silica gel, EtOAc) to give the title compound in 91% yield: 1H NMR (400 MHz, CDCl3) δ 1.70 (6H, s), 3.57 (1H, s), 3.87 (3H, s), 6.78–6.83 (2H, m), 7.87 (1H, dd, J 1.6, 6.6), 8.23 (1H, s), 8.69 (1H, s); MS (ES+) m/z 303 [M+H]+.

Workup

  1. customThe residue was purified by flash column chromatography (silica gel, EtOAc)

Sources & evidence

ORD record
ord-bbce9120f0624f10aa4d33cadf2adecf
Source dataset
uspto-grants-2006_02
Patent number
US07005431B2

Reaction notes

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