Phenylsilane → HCID 22623987, compound

HRID 279022Notes

Reaction equation

HRID 279022 reaction equation
C([O:4][N:5]1[C:14](=[O:15])[C:13]2[CH:16]=[C:17]([Br:19])[CH:18]=[C:11]3[C:12]=2[C:7](=[CH:8][CH:9]=[C:10]3[N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:6]1=[O:25])C=C.C1([SiH3])C=CC=CC=1>C(Cl)Cl.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>[Br:19][C:17]1[CH:18]=[C:11]2[C:10]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:9][CH:8]=[C:7]3[C:12]2=[C:13]([CH:16]=1)[C:14](=[O:15])[N:5]([OH:4])[C:6]3=[O:25]

Participants

5

Reactant 2

HCID 12752PhenylsilaneHCID 22623932HCID 22623932, compound

Product 1

HCID 22623987HCID 22623987, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 2-allyloxy-5-bromo-7-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.81 g, 2.0 mmol, from Example G2) in CH2Cl2 (40 mL) was added phenylsilane (0.32 g, 3.0 mmol) and Pd(PPh3)4 (0.050 g, 0.043 mmol). The reaction was stirred for 15 minutes, and the resulting precipitate removed by filtration, washed with CH2Cl2, and dried to give 0.60 g of the title compound, mp 234-235° C.

Workup

  1. customTo a 0° C.
  2. customthe resulting precipitate removed by filtration
  3. washwashed with CH2Cl2
  4. customdried

Sources & evidence

ORD record
ord-8064203f74c740a1b04371fc0e9138da
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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