Triethylsilane → HCID 10782159, compound

HRID 1069570Notes

Reaction equation

HRID 1069570 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-5893af4ff6aa4b3fbc373f78569b293b
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

Loading…