Trimethylsilyldiazomethane → HCID 178504169, compound

HRID 658407Notes

Reaction equation

HRID 658407 reaction equation
C([Li])CCC.[CH3:6][Si:7]([CH:10]=[N+:11]=[N-:12])([CH3:9])[CH3:8].[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]=[C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[F:36])[C:23]=1[C:24]#[N:25]>C1COCC1.CCOC(C)=O>[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]=[C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[F:36])[C:23]=1[C:24]1[N:25]=[N:12][NH:11][C:10]=1[Si:7]([CH3:9])([CH3:8])[CH3:6]

Participants

6

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 59026801HCID 59026801, compoundHCID 178418339Butyllithium

Product 1

HCID 178504169HCID 178504169, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

n-Butyllithium (28 μL, 2.5 M in THF, 0.07 mmol) was added to a solution of (trimethylsilyl)diazomethane (35 μL, 2.0 M in THF, 0.07 mmol) in THF (1 mL) at 0° C., and stirred for 20 minutes. 3-(2-Fluoro-4-iodo-phenylamino)-5-(2-fluoro-phenyl)-isonicotinonitrile (20 mg, 0.05 mmol) was added, and the resulting solution was stirred overnight at room temperature. The reaction solution was diluted with EtOAc and satd. NH4Cl, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 0 to 75% EtOAc in hexanes to afford the desired product (10 mg, 40%). LC-MS (M+H=548, obsd.=548).

Workup

  1. stirringthe resulting solution was stirred overnight at room temperature
  2. filtrationNH4Cl, and filtered through an Extrelut column
  3. washThe column was washed with EtOAc
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified via Biotage
  6. washeluting with a gradient of 0 to 75% EtOAc in hexanes

Sources & evidence

ORD record
ord-f0b30b48771642beb315dd2905a3e7e5
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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