4-Fluoro-3-(pyridin-3-yl)benzeneboronic acid → 2-[8-Fluoro-3-[4-fluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]-pyridin-7-yl]propan-2-ol

HRID 1180223Notes

Reaction equation

HRID 1180223 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:12]([O:15][Si](CC)(CC)CC)([CH3:14])[CH3:13])=[C:10]([F:11])[C:5]2=[N:4][CH:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][C:25]=1[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1>Cl>[F:11][C:10]1[C:5]2[N:6]([C:2]([C:27]3[CH:28]=[CH:29][C:24]([F:23])=[C:25]([C:33]4[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=4)[CH:26]=3)=[CH:3][N:4]=2)[CH:7]=[CH:8][C:9]=1[C:12]([OH:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 224735734-Fluoro-3-(pyridin-3-yl)benzeneboronic acidHCID 695489923-Bromo-8-fluoro-7-[2-(triethylsilyloxy)prop-2-yl]imidazo[1,2-alpha]pyridine

Product 1

HCID 100443692-[8-Fluoro-3-[4-fluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]-pyridin-7-yl]propan-2-ol

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

3-Bromo-8-fluoro-7-[2-(triethylsilyloxy)prop-2-yl]imidazo[1,2-α]pyridine was coupled with 4-fluoro-3-(pyridin-3-yl)phenylboronic acid as described in Example 1 and then deprotected by treatment with an ethanolic solution of 37% hydrochloric acid (5 drops in 2 ml of ethanol). After 18 h, the solution was concentrated in vacuo and purified by column chromatography on silica, to afford the title compound as a white amorphous solid: δH (360 MHz, CDCl3) 1.74 (6H, s), 7.20 (1H, t, J 7.0), 7.26-7.44 (2H, m), 7.54-7.62 (2H, m), 7.71 (1H, s), 7.90-7.93 (2H, m), 8.05 (1H, d, J 7.3), 8.65-8.66 (1H, m), 8.85 (1H, s); m/z (ES+) 366 (100%, [MH]+).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. custompurified by column chromatography on silica

Sources & evidence

ORD record
ord-a51276065f444ce18d92b029779bc3c4
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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