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

HRID 2184037Notes

Reaction equation

HRID 2184037 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([CH3:22])([CH3:21])[CH2:12][O:13][Si](CC)(CC)CC)=[N:10][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>>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:11]([CH3:21])([CH3:22])[CH2:12][OH:13])=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:26][C:25]=1[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1

Participants

3

Reactant 2

HCID 224735734-Fluoro-3-(pyridin-3-yl)benzeneboronic acidHCID 697085563-Bromo-7-(1,1-dimethyl-2-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

Product 1

HCID 101555492-[3-(4-Fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-alpha]pyrimidin-7-yl]-2-methylpropan-1-ol

Procedure

3-Bromo-7-(1,1-dimethyl-2-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine was coupled to 4-fluoro-3-(pyridin-3-yl)benzeneboronic acid (323 mg, 1.28 mmol) following the procedure in Example 65 and deprotected as described in Example 8 to give 2-[3-(4-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]-2-methylpropan-1-ol as a white powder: δH (360 MHz, CDCl3) 1.39 (6H, s), 3.54 (1H, t, J 7), 3.89 (1H, d, J 7), 6.99 (1H, d, J 7), 7.35-7.45 (2H, m), 7.51-7.60 (2H, m), 7.83 (1H, s), 7.90-7.94 (1H, m), 8.53 (1H, d, J 7), 8.68 (1H, dd, J 5 and 2), 8.83 (1H, s); m/z (ES+) 363 (M++H).

Sources & evidence

ORD record
ord-9f9e057db7674bf9a3edf67bc927992b
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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