Phenylsilane → HCID 22624003, compound

HRID 279040Notes

Reaction equation

HRID 279040 reaction equation
[C:1]([NH:4][C:5]1[C:10]2[C:11](=[O:24])[N:12]([O:20]CC=C)[C:13](=[O:19])[C:14]3=[CH:15][CH:16]=[C:17]([Cl:18])[C:8]([C:9]=23)=[C:7]([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:6]=1)(=[O:3])[CH3:2].C1([SiH3])C=CC=CC=1>ClCCl.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:1]([NH:4][C:5]1[C:10]2[C:11](=[O:24])[N:12]([OH:20])[C:13](=[O:19])[C:14]3=[CH:15][CH:16]=[C:17]([Cl:18])[C:8]([C:9]=23)=[C:7]([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 12752PhenylsilaneHCID 22624029HCID 22624029, compound

Product 1

HCID 22624003HCID 22624003, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-acetylamino-2-allyloxy-7-chloro-6-(pyrrolidin-1-yl)benzo[de]isoquinoline-1,3-dione (0.24 g, 0.6 mmol, from Example H4) and phenylsilane (0.13 g, 1.2 mmol) in 15 mL of dichloromethane was cooled to 15° C. and treated with tetrakis(triphenylphosphine)palladium (27 mg, 0.02 mmol). The reaction was stirred for 1 hour and the solvent removed in vacuo. The residue was dissolved in methanol, filtered, and evaporated in vacuo. The residue was stirred with ether to give a fine precipitate which was filtered, washed with ether, and dried in vacuo to give 0.1 g of the title compound, mp 152-154° C.

Workup

  1. customwas cooled to 15° C.
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in methanol
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. stirringThe residue was stirred with ether
  7. customto give a fine precipitate which
  8. filtrationwas filtered
  9. washwashed with ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-b7375c1811d3402a929ad300c8e900cf
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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