Trimethylsilyldiazomethane → HCID 178504168, compound

HRID 658410Notes

Reaction equation

HRID 658410 reaction equation
[Si:1]([CH:5]=[N+:6]=[N-:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[F:13][C:14]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:15]=1[NH:21][C:22]1[CH:29]=[N:28][CH:27]=[CH:26][C:23]=1[C:24]#[N:25]>CCOCC>[F:13][C:14]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:15]=1[NH:21][C:22]1[CH:29]=[N:28][CH:27]=[CH:26][C:23]=1[C:24]1[N:25]=[N:7][NH:6][C:5]=1[Si:1]([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 59026796HCID 59026796, compoundHCID 178418339Butyllithium

Product 1

HCID 178504168HCID 178504168, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of TMSdiazomethane (2 M, 90 μL, 0.18 mmol) in ether (2 mL) at 0° C., was added butyl lithium (2.5 M, 72 μL, 0.18 mmol) dropwise. The mixture was stirred for 20 min at 0° C. 3-[(2-fluoro-4-iodophenyl)amino]isonicotinonitrile (50 mg, 0.15 mmol) was then added into the solution. The reaction was allowed to warm to room temperature and proceed for three days. The mixture was diluted with ether and washed with saturated ammonium chloride solution, water, and dried over solid Na2SO4. The organic phase was concentrated, and the resulting residue was applied to chromatography in silica gel to give the desired product in 40% yield (27 mg). LC/MS [Method A: rt: 0.40 min; m/z: 454 (M+1)].

Workup

  1. temperatureto warm to room temperature
  2. waitproceed for three days
  3. washwashed with saturated ammonium chloride solution, water
  4. dry with materialdried over solid Na2SO4
  5. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-bee8378ba01f4c0ba0353243750e2bba
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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