Chlorotrimethylsilane → HCID 19035967, compound

HRID 263907Notes

Reaction equation

HRID 263907 reaction equation
[N:1]1[C:2]2[C:14](=[O:15])[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:3]=2[NH:4][C:5](=[O:7])[CH:6]=1.C(N(CC)CC)C.C[Si](Cl)(C)C.[C:28]1([Mg]Br)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[OH:15][C:14]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:2]2[N:1]=[CH:6][C:5](=[O:7])[NH:4][C:3]=2[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]1=2

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 190359769H-Indeno[1,2-b]pyrazine-3,9(4H)-dioneHCID 178418255HCID 178418255, compound

Product 1

HCID 19035967HCID 19035967, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

9H-Indeno[1,2-b]pyrazine-3,9(4H)-dione (2 g) was dissolved in dry THF (50 ml). Triethylamine (1.6 ml) was added and trimethylsilyl chloride (1.4 ml) dissolved in THF (10 ml) was added dropwise at room temperature. The mixture was stirred overnight and the precipitate filtered off. Phenylmagnesium bromide (20 mmol) in THF (10 ml) was subsequently added dropwise under nitrogen, and the resulting mixture stirred at room temperature for 3 days. Subsequent evaporation followed by addition of water and addition of HCl (1N) to slightly acidic solution resulted in precipitation of yellow crystals (2.7 g). The precipitate was purified on silica gel column using methylene chloride/methanol (9/1) as eluent resulting in 1.2 g pure title compound. M.p.>270° C. The MS showed the molecular ion 276. 1H-NMR (DMSO-d6, δ): 6.39 (s, 1H), 7.15-7.5 (m, 8H), 7.82 (s+m, 2H), 12.6 (s, 1H).

Workup

  1. additionwas added dropwise at room temperature
  2. filtrationthe precipitate filtered off
  3. stirringthe resulting mixture stirred at room temperature for 3 days
  4. customSubsequent evaporation
  5. additionfollowed by addition of water and addition of HCl (1N) to slightly acidic solution

Sources & evidence

ORD record
ord-17fb3935180d4a31ad31e085eb62395f
Source dataset
uspto-grants-1997_07
Patent number
US05646146

Reaction notes

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