Hydrochloric Acid → HCID 178458506, compound

HRID 278116Notes

Reaction equation

HRID 278116 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[N:15])[CH:12]=2)[C:7]([C:16](=[O:19])[CH2:17][CH3:18])=[C:6]1[CH2:20][CH3:21].C[Sn]([N:30]=[N+:31]=[N-:32])(C)C.Cl>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]3[NH:32][N:31]=[N:30][N:15]=3)[CH:12]=2)[C:7]([C:16](=[O:19])[CH2:17][CH3:18])=[C:6]1[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5104973Azido(trimethyl)stannaneHCID 22627454HCID 22627454, compound

Product 1

HCID 178458506HCID 178458506, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-(2-chlorobenzyl)-2-ethyl-3-propionylindole-6-carbonitrile (107 mg) in xylene (5 ml) was added trimethyltin azide (190 mg), and the mixture was stirred at 120° C. for 14 hours. The resulting mixture was poured into 1N HCl and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 20% methanol in chloroform to give 1-(2-chlorobenzyl)-2-ethyl-3-propionyl-6-(1H-tetrazol-5-yl)indole (77 mg) as a solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with 20% methanol in chloroform

Sources & evidence

ORD record
ord-eb71bb64643b495980ccc3b5146b2076
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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