Dimethylformamide → 4-Fluoro-1-(2-methoxypyridin-4-yl)-1-(3-(pyrazin-2-yl)phenyl)-1H-isoindol-3-amine acetate

HRID 1662250Notes

Reaction equation

HRID 1662250 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([O:25][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([Sn](CCCC)(CCCC)[C:32]1[CH:37]=[N:36][CH:35]=[CH:34][N:33]=1)CCC.CN(C=[O:50])C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:21]([OH:25])(=[O:50])[CH3:20].[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]=[CH:23][N:22]=[C:21]([O:25][CH3:26])[CH:20]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:32]2[CH:37]=[N:36][CH:35]=[CH:34][N:33]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27373162-(Tributylstannyl)pyrazineHCID 585794981-(3-Bromophenyl)-4-fluoro-1-(2-methoxypyridin-4-yl)-1H-isoindol-3-amine

Product 1

HCID 674190584-Fluoro-1-(2-methoxypyridin-4-yl)-1-(3-(pyrazin-2-yl)phenyl)-1H-isoindol-3-amine acetateYield 48.5%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

1-(3-Bromophenyl)-4-fluoro-1-(2-methoxypyridin-4-yl)-1H-isoindol-3-amine (0.150 g, 0.36 mmol), 2-(tributylstannyl)pyrazine (0.120 mL, 0.38 mmol), tetrakis(triphenylphosphine)palladium(0) (0.042 g, 0.04 mmol) and DMF (4 mL) were put in microwave vial and irradiated in a microwave reactor at 150° C. for 20 min. The resulting product mixture was filtered and purified by preparative-HPLC to give the title compound 0.083 g, (48.5% yield).

Workup

  1. customirradiated in a microwave reactor at 150° C. for 20 min
  2. filtrationThe resulting product mixture was filtered
  3. custompurified by preparative-HPLC

Sources & evidence

ORD record
ord-51d30279ae374cfe8305ae54e53f4d82
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

Loading…