Triethylsilane → HCID 57426204, compound

HRID 641411Notes

Reaction equation

HRID 641411 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)[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[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][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:14][NH:15]2)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 57426203HCID 57426203, compound

Product 1

HCID 57426204HCID 57426204, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (11 mL, 68 mmol) was added to a solution of ethyl 4-(4-nitro-1H-indol-3-yl)-4-oxobutanoate from Step A (960 mg, 3.31 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 94:6, to give the title compound. MS: m/z=279 (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-1b3046424ba841f288dfbc051470fa53
Source dataset
uspto-grants-2010_04
Patent number
US07696192B2

Reaction notes

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