Hexane → N-tert-butyl-N-dimethylsilyl-2,5-dimethyl-6H-indeno[2,3-b]indol-6-amine

HRID 1581732Notes

Reaction equation

HRID 1581732 reaction equation
[Li]CCCC.CCCCCC.[CH3:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([CH3:22])=[CH:19][CH:20]=2)[C:15]2[C:23]3[C:28]([CH2:29][C:14]1=2)=[CH:27][CH:26]=[CH:25][CH:24]=3.[C:30]([NH:34][Si:35]([CH3:38])([CH3:37])Cl)([CH3:33])([CH3:32])[CH3:31]>CCOCC>[CH3:37][SiH:35]([N:34]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:29]1[C:14]2[N:13]([CH3:12])[C:21]3[C:16]([C:15]=2[C:23]2[C:28]1=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][C:18]([CH3:22])=[CH:19][CH:20]=3)[CH3:38]

Participants

6

Reactant 4

HCID 8058HexaneHCID 11205972t-ButylaminodimethylsilylchlorideHCID 155337292,5-Dimethyl-5,6-dihydroindeno[2,1-b]indoleHCID 178418339Butyllithium

Product 1

HCID 131724426N-tert-butyl-N-dimethylsilyl-2,5-dimethyl-6H-indeno[2,3-b]indol-6-amineYield 106.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6.66 mL of n-BuLi 2.5 M in hexane (16.65 mmol) were added dropwise at 0° C. to a solution of 3.53 g of N-methyl-2-methyl-5,6-dihydroindeno[2,1-b]indole (Mw=233.32, purity 99.0%, 15.13 mmol) in Et2O. At the end of the addition, the reaction mixture was allowed to warm up to room temperature and stirred for two hours. Subsequently, 3.34 g of (tert-butylamino)dimethylchlorosilane (Mw=165.74, purity 75.0% mol., d=0.887, 20.17 mmol) were added at 0° C. to the Li salt suspension and the resulting mixture was allowed to warm up to room temperature. After three hours stirring, the solvents were evaporated under reduced pressure and the residue was dissolved in 50 mL of toluene, obtaining a dark brown suspension, which was filtered. The filtrate was evaporated to dryness under reduced pressure, obtaining 5.86 g of a dark brown oil, which resulted to be 86.5% wt. pure (calculated by 1H-NMR). Yield=92.4%.

Workup

  1. additionAt the end of the addition
  2. temperatureto warm up to room temperature
  3. stirringAfter three hours stirring
  4. customthe solvents were evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in 50 mL of toluene
  6. customobtaining a dark brown suspension, which
  7. filtrationwas filtered
  8. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c47925e7385446ac880b8ea7e455b0ab
Source dataset
uspto-grants-2004_05
Patent number
US06730754B2

Reaction notes

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