Potassium Carbonate → 5-(3-(3-Amino-1-(2,6-dimethylpyridin-4-yl)-4-fluoro-1H-isoindol-1 yl)phenyl)nicotinonitrile

HRID 1662243Notes

Reaction equation

HRID 1662243 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:19]3[CH:24]=[C:23]([CH3:25])[N:22]=[C:21]([CH3:26])[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:5]=[CH:6][CH:7]=1.[C:27]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[N:33][CH:34]=1)#[N:28].C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[NH2:18][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[C:8]([C:4]2[CH:3]=[C:2]([C:31]3[CH:32]=[N:33][CH:34]=[C:29]([CH:30]=3)[C:27]#[N:28])[CH:7]=[CH:6][CH:5]=2)([C:19]2[CH:20]=[C:21]([CH3:26])[N:22]=[C:23]([CH3:25])[CH:24]=2)[N:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 450795765-Cyanopyridine-3-boronic acidHCID 674184801-(3-bromophenyl)-1-(2,6-dimethylpyridin-4-yl)-4-fluoro-1H-isoindol-3-amine

Product 1

HCID 462066445-(3-(3-Amino-1-(2,6-dimethylpyridin-4-yl)-4-fluoro-1H-isoindol-1 yl)phenyl)nicotinonitrileYield 53%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

The title compound was synthesized as described for Example 12 in 53% yield starting from 1-(3-bromophenyl)-1-(2,6-dimethylpyridin-4-yl)-4-fluoro-1H-isoindol-3-amine (104.8 mg, 0.26 mmol), 5-cyanopyridin-3-ylboronic acid (37.8 mg, 0.26 mmol), PdCl2(dppf)-CH2Cl2 adduct (20.9 mg, 0.03 mmol), and K2CO3 (aq) (0.38 mL, 0.77 mmol).

Sources & evidence

ORD record
ord-ea2d4c2074f54ac39c59ea31c93d7fc4
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

Loading…