Triethylsilane → HCID 10782159, compound

HRID 2292767Notes

Reaction equation

HRID 2292767 reaction equation
[CH3:1][C:2]1[N:3]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:4]2[C:9]([C:10]=1[CH:11](O)[C:12]([NH2:14])=[O:13])=[CH:8][C:7]([N+:16]([O-:18])=[O:17])=[CH:6][CH:5]=2.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH3:1][C:2]1[N:3]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:4]2[C:9]([C:10]=1[CH2:11][C:12]([NH2:14])=[O:13])=[CH:8][C:7]([N+:16]([O-:18])=[O:17])=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 10783257HCID 10783257, compound

Product 1

HCID 10782159HCID 10782159, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 0.927 g (2.7 mmol) of 2-methyl-5-nitro-1-(phenylmethyl)-1H-indole-3-glycolic acid amide in 15 mL of trifluoroacetic acid was treated with 1.0 mL (6.0 mmol) of triethylsilane and the mixture stirred for 1.0 hour. After concentrating at reduced pressure, the residue was chromatographed on silca (eluted with EtOAc) and crystallized from MeOH/CH2Cl2 to give 455 mg (52% yield) of 2-methyl-5-nitro-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 189°-192° C.

Workup

  1. concentrationAfter concentrating at reduced pressure
  2. customthe residue was chromatographed on silca (eluted with EtOAc)
  3. customcrystallized from MeOH/CH2Cl2

Sources & evidence

ORD record
ord-9fbd8d16745444cbb4e855d63fa4a94e
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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