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

HRID 1696357Notes

Reaction equation

HRID 1696357 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]>C(O)(C(F)(F)F)=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

Triethylsilane (13 mL, 80.6 mmol) was added to a solution of methyl (4-nitro-1H-indol-3-yl)(oxo)acetate from Step A (1.00 g, 4.03 mmol) in TFA (15 mL). After 3 h, the reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with a gradient of CHCl3:MeOH—100:0 to 98:2, to give the title compound. MS: m/z=237 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with a gradient of CHCl3

Sources & evidence

ORD record
ord-4aa04db89b5544b6b9b5a6e80e04dd9b
Source dataset
uspto-grants-2012_04
Patent number
US08163752B2

Reaction notes

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