Azido(trimethyl)stannane → HCID 178477328, compound

HRID 1707659Notes

Reaction equation

HRID 1707659 reaction equation
[C:1]([C:3]1[CH:7]=[C:6]([CH3:8])[N:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:30]=[CH:29][C:14]([CH2:15][N:16]2[C:20]3=[N:21][CH:22]=[CH:23][C:24]([CH3:25])=[C:19]3[N:18]=[C:17]2[S:26][CH2:27][CH3:28])=[CH:13][CH:12]=1)#[N:2].C[Sn]([N:35]=[N+:36]=[N-:37])(C)C>C1(C)C(C)=CC=CC=1>[CH2:9]([N:5]1[C:6]([CH3:8])=[CH:7][C:3]([C:1]2[NH:37][N:36]=[N:35][N:2]=2)=[C:4]1[C:11]1[CH:30]=[CH:29][C:14]([CH2:15][N:16]2[C:20]3=[N:21][CH:22]=[CH:23][C:24]([CH3:25])=[C:19]3[N:18]=[C:17]2[S:26][CH2:27][CH3:28])=[CH:13][CH:12]=1)[CH3:10]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 189619153-[4-(3-cyano-1-ethyl-5-methyl-2-pyrrolyl)benzyl]-2-ethylthio-7-methyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 178477328HCID 178477328, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
125 °C

Procedure

To a mixture of 3-[4-(3-cyano-1-ethyl-5-methyl-2-pyrrolyl)benzyl]-2-ethylthio-7-methyl-3H-imidazo[4,5-b]pyridine (1.52 g) in xylene (15 ml) was added trimethyltin azid (2.26 g) under nitrogen atmosphere, and stirred at 125° C. for 24 hours. The mixture was concentrated in vacuo. To the residue was added methanol and conc. hydrochloric acid (1 ml). The mixture was stirred at ambient temperature for one hour and concentrated in vacuo. The residue was diluted with methanol. The mixture was adjusted to pH4 with 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 subsequent crystallization from methyl cyanide to give amorphous powder (1.47 g) of 3-[4-[1-ethyl-5-methyl-3-(1H-tetrazol-5-yl)-2-pyrrolyl]benzyl]-2-ethylthio-7-methyl-3H-imidazo[4,5-b]pyridine.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionTo the residue was added methanol and conc. hydrochloric acid (1 ml)
  3. stirringThe mixture was stirred at ambient temperature for one hour
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with methanol
  6. customThe organic layer was separated
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel (elution by dichloromethane/methanol=15/1) and subsequent crystallization from methyl cyanide

Sources & evidence

ORD record
ord-e876b543ec9f42b6a3ef98e80a40896d
Source dataset
uspto-grants-1994_10
Patent number
US05354759

Reaction notes

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