Azobisisobutyronitrile → HCID 19697337, compound

HRID 862381Notes

Reaction equation

HRID 862381 reaction equation
Br[CH:2]1[CH:10]([F:11])[CH2:9][C:8]2[C:7](=[O:12])[N:6]([C:13]3[CH:18]=[C:17]([O:19][CH2:20][C:21]#[CH:22])[C:16]([Cl:23])=[CH:15][C:14]=3[F:24])[C:5](=[O:25])[C:4]=2[CH2:3]1.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[Cl:23][C:16]1[C:17]([O:19][CH2:20][C:21]#[CH:22])=[CH:18][C:13]([N:6]2[C:7](=[O:12])[C:8]3[CH2:9][CH:10]([F:11])[CH2:2][CH2:3][C:4]=3[C:5]2=[O:25])=[C:14]([F:24])[CH:15]=1

Participants

4

Reactant 2

HCID 6547AzobisisobutyronitrileHCID 19697339HCID 19697339, compound

Product 1

HCID 19697337HCID 19697337, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 526 mg (1.22 mmol) of 5-bromo-2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-6-fluoro4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione, 822 mL of n-tributyltin hydride (3.06 mmol), and a catalytic amount of AIBN (2,2'-azobis[2-methylpropanenitrile]) in 20 mL of benzene was warmed under reflux for 1h. The mixture was then concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel eluting with a 1:4 v:v mixture of ethyl acetate and n-hexane to give 332 mg of the title product of Example 5, a compound of the invention, as a colorless oily film. 1H NMR (CDCl3, 300 MHz) δ 1.8-2.0 (m, 2H), 2.3-2.9 (m, 5H), 4.8 (d, 2H), 5.22 (dm, J=50 Hz, 1H), 7.0 (d, 1H), 7.3 (d,1H).

Workup

  1. temperatureunder reflux for 1h
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customThe crude product was purified by flash chromatography over silica gel eluting with a 1:4 v
  4. additionv mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-a4faeb94c52b4cbdb6ad55f08325f9b9
Source dataset
uspto-grants-1998_02
Patent number
US05719104

Reaction notes

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