Tributylstannane → HCID 178517035, compound

HRID 2213680Notes

Reaction equation

HRID 2213680 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[C:13]([C:15]1[NH:16][CH:17]=[CH:18][CH:19]=1)C)#[N:2].C([SnH](CCCC)CCCC)CCC.[N-:33]=[N+:34]=[N-:35].[Na+]>C1(C)C=CC=CC=1.CO>[NH:2]1[C:1]([C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[C:6]3=[CH:13][C:15]2[NH:16][CH:17]=[CH:18][CH:19]=2)=[N:35][N:34]=[N:33]1

Participants

6

Reactant 3

HCID 5948TributylstannaneHCID 33557Sodium AzideHCID 695452315-Cyano-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one

Product 1

HCID 178517035HCID 178517035, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 5-cyano-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one (100 mg, 0,42 mmol) in toluene was treated with tributyltin hydride (0.68 g, 2.1 mmol) and NaN3 (0.39 g, 2.52 mmol). The reaction mixture was refluxed overnight. Concentration afforded a residue which was dissolved in methanol and left at ambient temperature overnight. An orange-colored solid formed, which was filtered and dried in vacuo to afford 5-tetrazol-5-yl-3-[(pyrrol-2-yl)methylene]indolin-2-one; (29 mg) as an orange solid; 1H NMR (400 MHz, DMSO-d6) δ 6.22 (s, 1H), 6.90 (s, 1H), 7.08 (d, 1H), 7.20 (s, 1H), 7.80 (m, 1H), 7.84 (s, 1H), 8.14 (s, 1H), 11.22 (s, 1H) ppm.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationConcentration
  3. customafforded a residue which
  4. customAn orange-colored solid formed
  5. filtrationwhich was filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8f683fb88a204bf1b094f0da48033d4e
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

Loading…