Triethylsilane → methyl (4-nitro-2,3-dihydro-1H-indol-3-yl)-acetate

HRID 74572

Reaction equation

HRID 74572 reaction equation
C([SiH](CC)CC)C.[N+:8]([C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[C:13]([C:20](=O)[C:21]([O:23][CH3:24])=[O:22])=[CH:14][NH:15]2)([O-:10])=[O:9]>FC(F)(F)C(O)=O>[N+:8]([C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:14][NH:15]2)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 10243717Methyl (4-nitro-1H-indol-3-yl)(oxo)acetate

Product 1

HCID 10243182methyl (4-nitro-2,3-dihydro-1H-indol-3-yl)-acetate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Under an argon atmosphere 16 mL (0.10 mmol) triethylsilane were slowly added dropwise to 2.3 g (9.3 mmol) methyl (4-nitro-1H-indol-3-yl)-oxo-acetate in 18 mL trifluoroacetic acid while cooling with ice. Then the mixture was stirred for a further 3 h at RT and evaporated down. The residue was dried and then triturated with diisopropylether, suction filtered and dried in the air.

Workup

  1. temperaturewhile cooling with ice
  2. customevaporated down
  3. customThe residue was dried
  4. customtriturated with diisopropylether, suction
  5. filtrationfiltered
  6. customdried in the air

Sources & evidence

ORD record
ord-4dc15c7d857a4497b86d2906e813aebc
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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