3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester → 8-(3,6-dihydro-2H-pyran-4-yl)-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 451495Notes

Reaction equation

HRID 451495 reaction equation
Br[C:2]1[C:3]2[N:4]([N:9]=[C:10]([NH2:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[O:13]1[CH2:18][CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH2:15][CH2:14]1>>[O:13]1[CH2:14][CH:15]=[C:16]([C:2]2[C:3]3[N:4]([N:9]=[C:10]([NH2:12])[N:11]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=2)[CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 214643388-Bromo-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 673431668-(3,6-dihydro-2H-pyran-4-yl)-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Procedure

Prepared in analogy to example 160b, starting from 8-bromo-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The title compound was obtained a light brown solid (yield: 55%) after column chromatography on silica gel using ethyl acetate as eluent.

Workup

  1. customPrepared in analogy to example 160b

Sources & evidence

ORD record
ord-e7f202f0758342bc818a194ef5192322
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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