4-Methylbenzaldehyde → [3-(2-Chloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]-p-tolyl-methanol

HRID 2252320Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:9][N:10]=2)[CH:7]=1.C([Mg]Cl)(C)C.[CH3:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1>C1COCC1>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:8]1[N:6]2[CH:7]=[C:2]([CH:28]([C:27]3[CH:30]=[CH:31][C:24]([CH3:23])=[CH:25][CH:26]=3)[OH:29])[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

In a flame-dried flash under nitrogen a solution of 6-bromo-3-(2-chloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridine (205 mg, 0.66 mmol) in THF (2.5 mL) was cooled to 0° C. A solution of isopropylmagnesium chloride (1.3 eq) was added dropwise, followed by 4-methylbenzaldehyde (1 equivalent), and the resulting mixture was warmed to 50° C. for 3 hours. The reaction was cooled and quenched with water/ethyl acetate. The organic layer was separated, concentrated in vacuo, and the residue purified by flash chromatography (eluting with 80% ethyl acetate/hexane) to give the title compound (67 mg, 29%). MS (M+1)=350.5.

Workup

temperatureThe reaction was cooled
customquenched with water/ethyl acetate
customThe organic layer was separated
concentrationconcentrated in vacuo
customthe residue purified by flash chromatography (eluting with 80% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-57ca661e70024ea4bd78d6e7709240d7
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07321040B2

Reaction notes

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