Azido(trimethyl)stannane → HCID 178477327, compound

HRID 1707658Notes

Reaction equation

HRID 1707658 reaction equation
[Br:1][C:2]1([C:10]2[CH:29]=[CH:28][C:13]([CH2:14][N:15]3[C:19]4=[N:20][CH:21]=[CH:22][C:23]([CH3:24])=[C:18]4[N:17]=[C:16]3[S:25][CH2:26][CH3:27])=[CH:12][CH:11]=2)[CH2:6][C:5]([C:7]#[N:8])=[CH:4][N:3]1[CH3:9].C[Sn]([N:34]=[N+:35]=[N-:36])(C)C>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1([C:10]2[CH:29]=[CH:28][C:13]([CH2:14][N:15]3[C:19]4=[N:20][CH:21]=[CH:22][C:23]([CH3:24])=[C:18]4[N:17]=[C:16]3[S:25][CH2:26][CH3:27])=[CH:12][CH:11]=2)[CH2:6][C:5]([C:7]2[NH:36][N:35]=[N:34][N:8]=2)=[CH:4][N:3]1[CH3:9]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 18961922HCID 18961922, compound

Product 1

HCID 178477327HCID 178477327, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a stirred solution of 3-[4-(2-bromo-4-cyano-1-methyl-2-pyrrolyl)benzyl]-2-ethylthio-7-methyl-3H-imidazo[4,5-b]pyridine (1.30 g) in xylene (15 ml) was added trimethyltin azide (1.72 g) at 125° C., stirred at the same temperature for 36 hours under nitrogen atmosphere, and the mixture was evaporated in vacuo. The residue was diluted with methanol and conc. hydrochloric acid (1 ml) was added therein. The mixture was stirred for 1 hour at ambient temperature. The mixture was concentrated in vacuo. The residue was diluted with methanol and adjusted to pH4 with aqueous 1N sodium hydroxide. The organic layer was separated, and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel (elution by dichloromethane/methanol=15/1) and by preparative thin layer chromatography (elution by dichloromethane/methanol=8/1) to yield 3-[4-[2-bromo-1-methyl-4-(1H-tetrazol-5yl)-2-pyrrolyl]benzyl-2-ethylthio-7-methyl-3H-imidazo[4,5-b]pyridine (691 mg) as a colorless amorphous solid.

Workup

  1. customthe mixture was evaporated in vacuo
  2. additionThe residue was diluted with methanol and conc. hydrochloric acid (1 ml)
  3. additionwas added
  4. stirringThe mixture was stirred for 1 hour at ambient temperature
  5. concentrationThe mixture was concentrated in vacuo
  6. additionThe residue was diluted with methanol
  7. customThe organic layer was separated
  8. customevaporated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel (elution by dichloromethane/methanol=15/1) and by preparative thin layer chromatography (elution by dichloromethane/methanol=8/1)

Sources & evidence

ORD record
ord-e755cb40dea44b2bb84fa020d07e0436
Source dataset
uspto-grants-1994_10
Patent number
US05354759

Reaction notes

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