Potassium Carbonate → 4-Fluoro-1-[3-(5-pyrimidinyl)phenyl]-1-[2-(trifluoromethyl)-4-pyridinyl]-1H-isoindol-3-amine

HRID 1662241Notes

Reaction equation

HRID 1662241 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]([F:28])([F:27])[F: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.[N:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[N:31][CH:30]=1.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>[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:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:33]2[CH:34]=[N:29][CH:30]=[N:31][CH:32]=2)[CH:3]=1)[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([C:25]([F:26])([F:28])[F:27])[CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 674290791-(3-Bromophenyl)-4-fluoro-1-[2-(trifluoromethyl)-4-pyridinyl]-1H-isoindol-3-amine

Product 1

HCID 462066424-Fluoro-1-[3-(5-pyrimidinyl)phenyl]-1-[2-(trifluoromethyl)-4-pyridinyl]-1H-isoindol-3-amineYield 46%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

The title compound was synthesized as described for Example 12 in 46% yield starting from 1-(3-bromophenyl)-4-fluoro-1-(2-(trifluoromethyl)pyridin-4-yl)-1H-isoindol-3-amine (56.2 mg, 0.12 mmol), pyrimidin-5-ylboronic acid (17.0 mg, 0.14 mmol), PdCl2(dppf)-CH2Cl2 adduct (10.2 mg, 0.01 mmol), K2CO3 (aq) (0.19 mL, 0.37 mmol).

Sources & evidence

ORD record
ord-67ae0dd7e93f43e8b1d8b84f1ea5077b
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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