Dimethylformamide → HCID 178420724, compound

HRID 1446682Notes

Reaction equation

HRID 1446682 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[CH:10][N:11]=[C:5]2[CH:4]=1)#[CH:2].C[Si]([N:16]=[N+:17]=[N-:18])(C)C.CN(C=O)C>[Cu]I.CO>[NH:16]1[CH:2]=[C:1]([C:3]2[CH:8]=[CH:7][N:6]3[CH:9]=[CH:10][N:11]=[C:5]3[CH:4]=2)[N:18]=[N:17]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 78378AzidotrimethylsilaneHCID 76849545908269-32-9

Product 1

HCID 178420724HCID 178420724, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

Combine 7-ethynyl-imidazo[1,2-a]pyridine (1.10 g, 7.74 mmol), copper (I) iodide (0.074 g, 0.387 mmol), and trimethylsilyl azide (1.53 mL, 11.61 mmol) in a 9:1 mixture of DMF:methanol (13.8 mL) in a pressure flask. Seal the flask with a Teflon screw cap and heat the reaction mixture to 100° C., stir overnight (15 hours), and cool to room temperature. Concentrate the mixture to dryness in vacuo. Slurry the resulting solid into dichloromethane and filter through Celite® 521. Concentrate the solution in vacuo to an orange solid. Purify by column chromatography (ethyl acetate→5% methanol in dichloromethane→8% methanol in dichloromethane) to afford product (0.82 g, 57%). MS(ES), m/z 186 (M+1).

Workup

  1. customscrew cap
  2. temperaturecool to room temperature
  3. concentrationConcentrate the mixture to dryness in vacuo
  4. filtrationfilter through Celite® 521
  5. concentrationConcentrate the solution in vacuo to an orange solid
  6. customPurify by column chromatography (ethyl acetate→5% methanol in dichloromethane→8% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f1007d148df4422382a2af1889a9a986
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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