Azido(trimethyl)stannane → HCID 178497409, compound

HRID 391402Notes

Reaction equation

HRID 391402 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].[N:15]([Sn](C)(C)C)=[N+:16]=[N-:17]>C1(C)C=CC=CC=1>[CH3:14][O:13][C:6]1[CH:5]=[CH:4][C:3]([C:1]2[NH:17][N:16]=[N:15][N:2]=2)=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 18464789Methyl 5-cyano-2-methoxybenzoate

Product 1

HCID 178497409HCID 178497409, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of methyl 5-cyano-2-methoxybenzoate (0.87 g, 4.5 mmol) in toluene (4 mL) was treated with azidotrimethyltin (1.85 g, 9.0 mmol) and heated at reflux overnight. After cooling to room temperature, the solvents were evaporated. The crude product was dissolved in ethyl acetate, washed with brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (5% methanol/methylene chloride) afforded 0.78 g (75%). LC/MS (HPLC method 3): tR=1.66 min, 235.05 (MH)+.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customthe solvents were evaporated
  4. dissolutionThe crude product was dissolved in ethyl acetate
  5. washwashed with brine (2×)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customColumn chromatography on silica gel (5% methanol/methylene chloride) afforded 0.78 g (75%)

Sources & evidence

ORD record
ord-e496138d55444f21b535154ebed80644
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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