(Pyrimidin-5-yl)boronic acid → 4-Fluoro-1-(5-methoxy-4,6-dimethylpyridin-2-yl)-1-(2-(pyrimidin-5-yl)pyridin-4-yl)-1H-isoindol-3-amine

HRID 1662257Notes

Reaction equation

HRID 1662257 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]2([C:19]3[CH:24]=[C:23]([CH3:25])[C:22]([O:26][CH3:27])=[C:21]([CH3:28])[N:20]=3)[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:18])=[N:9]2)[CH:5]=[CH:4][N:3]=1.[N:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[N:31][CH:30]=1>>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[C:10]([NH2:18])=[N:9][C:8]2([C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([O:26][CH3:27])=[C:21]([CH3:28])[N:20]=1)[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:33]2[CH:34]=[N:29][CH:30]=[N:31][CH:32]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 585794841-(2-Bromopyridin-4-yl)-4-fluoro-1-(5-methoxy-4,6-dimethylpyridin-2-yl)-1H-isoindol-3-amine

Product 1

HCID 462020854-Fluoro-1-(5-methoxy-4,6-dimethylpyridin-2-yl)-1-(2-(pyrimidin-5-yl)pyridin-4-yl)-1H-isoindol-3-amineYield 7%

Procedure

The title compound was synthesized as described in Example 33 in 7% yield starting from 1-(2-Bromopyridin-4-yl)-4-fluoro-1-(5-methoxy-4,6-dimethylpyridin-2-yl)-1H-isoindol-3-amine (200 mg, 0.45 mmol) and pyrimidin-5-ylboronic acid (61.8 mg, 0.50 mmol).

Sources & evidence

ORD record
ord-d16a9b7d10e44265954501fe1586e53b
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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