5-Cyanopyridine-3-boronic acid → 5-(3-(3-Amino-4-fluoro-1-(2-methylpyridin-4-yl)-1H-isoindol-1-yl)-4-fluorophenyl)nicotinonitrile

HRID 1662227Notes

Reaction equation

HRID 1662227 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:26])=[C:6]([C:8]2([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[CH: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:7]=1.[C:27]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[N:33][CH:34]=1)#[N:28]>>[NH2:18][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[C:8]([C:6]2[CH:7]=[C:2]([C:31]3[CH:32]=[N:33][CH:34]=[C:29]([CH:30]=3)[C:27]#[N:28])[CH:3]=[CH:4][C:5]=2[F:26])([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[CH:20]=2)[N:9]=1

Participants

3

Reactant 2

HCID 450795765-Cyanopyridine-3-boronic acidHCID 585794991-(5-Bromo-2-fluorophenyl)-4-fluoro-1-(2-methylpyridin-4-yl)-1H-isoindol-3-amine

Product 1

HCID 462056395-(3-(3-Amino-4-fluoro-1-(2-methylpyridin-4-yl)-1H-isoindol-1-yl)-4-fluorophenyl)nicotinonitrileYield 38%

Procedure

The title compound was synthesized as described for Example 1 in 38% yield, starting from 1-(5-bromo-2-fluorophenyl)-4-fluoro-1-(2-methylpyridin-4-yl)-1H-isoindol-3-amine (80 mg, 0.19 mmol) and 5-cyanopyridin-3-ylboronic acid (37.1 mg, 0.25 mmol).

Sources & evidence

ORD record
ord-aa1723831e0a46da8881a713608f50c5
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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