Dichloromethane → 7-Amino-2-methyl-4-[(E)-2-phenylethenyl]-2,3-dihydro-1H-isoindol-1-one

HRID 511299Notes

Reaction equation

HRID 511299 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5](Br)=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2.[C:14]1(/[CH:20]=[CH:21]/B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].ClCCl>O1CCOCC1.O.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]>[NH2:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:21]=[CH:20]/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 5702628Styrylboronic acidHCID 534084597-Amino-4-bromo-2-methylisoindolin-1-one

Product 1

HCID 672555947-Amino-2-methyl-4-[(E)-2-phenylethenyl]-2,3-dihydro-1H-isoindol-1-one

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 7-amino-4-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one (1.0 g, 4.1 mmol), E-phenylethenylboronic acid (921 mg, 6.22 mmol), potassium carbonate (1.72 g, 12.4 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (169 mg, 0.207 mmol) in 10 mL 1,4-Dioxane and 2.5 mL H2O was irradiated in a microwave reactor at 100° C. for 30 minutes. The crude mixture was partitioned between EtOAc and sat. NaHCO3. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was used in the next step without further purification. MS (ES+): m/z 265.31 (100) [MH+]; HPLC: tR=1.24 min (UPLC, Analytical).

Workup

  1. customwas irradiated in a microwave reactor at 100° C. for 30 minutes
  2. customThe crude mixture was partitioned between EtOAc and sat. NaHCO3
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-0341ecb31698462ebb2711990adc9a64
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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