Phenylsilane → HCID 22623987, compound

HRID 567033Notes

Reaction equation

HRID 567033 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 phenysilane (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-1f011762d2bf4600ab1bf814ea2b9de4
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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