2-Methylphenyl boronic acid → 5-(benzyloxy)-1-o-tolyl-1H-imidazo[4,5-b]pyridine

HRID 1890295Notes

Reaction equation

HRID 1890295 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[NH:15][CH:16]=[N:17][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([CH3:27])[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.C(OC1N=C2N(C3C=CC=CC=3C)C=NC2=CC=1)C1C=CC=CC=1>>[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[N:15]=[CH:16][N:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH3:27])[C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 27332672-Methylphenyl boronic acidHCID 673129085-(benzyloxy)-3-o-tolyl-3H-imidazo[4,5-b]pyridineHCID 178420377HCID 178420377, compound

Product 1

HCID 673127605-(benzyloxy)-1-o-tolyl-1H-imidazo[4,5-b]pyridine

Procedure

From 5-(benzyloxy)-3H-imidazo[4,5-b]pyridine and o-tolylboronic acid, prepared in a similar manner as the one described in Example 1.25, Step A, 5-(benzyloxy)-3-o-tolyl-3H-imidazo[4,5-b]pyridine and 5-(benzyloxy)-1-o-tolyl-1H-imidazo[4,5-b]pyridine were obtained, which was then dissolved in DCM and diluted with excess sulfuric acid. The resulting solution was stirred for 30 minutes at room temperature then acidified with the addition of 1 M aqueous hydrochloric acid. The solvent was removed from the organic layer and the residue was purified via preparative HPLC to give the title compound. LCMS m/z=225.9 [M+H]+.

Sources & evidence

ORD record
ord-1796afd764654ab9a73480585e0eb3d8
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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