Toluene → HCID 59320155, compound

HRID 2380834Notes

Reaction equation

HRID 2380834 reaction equation
[Cl:1][C:2]1[CH:18]=[N:17][CH:16]=[CH:15][C:3]=1[C:4]([NH:6][NH:7][C:8]1[CH:13]=[C:12]([I:14])[CH:11]=[CH:10][N:9]=1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[Si](N=[N+]=[N-])(C)C.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:18]=[N:17][CH:16]=[CH:15][C:3]=1[C:4]1[N:9]2[CH:10]=[CH:11][C:12]([I:14])=[CH:13][C:8]2=[N:7][N:6]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68716304HCID 68716304, compound

Product 1

HCID 59320155HCID 59320155, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-chloro-N′-(4-iodopyridin-2-yl)isonicotinohydrazide (1.53 g, 4.08 mmol) and polymer supported triphenyl phosphine (2.83 g, 6.19 mmol) in tetrahydrofuran (35 mL) was added trimethylsilylazide (0.82 mL, 6.20 mmol) and a 40% solution of diethyl azodicarboxylate in toluene (3.40 mL, 7.42 mmol) and it was stirred in an orbital stirrer at room temperature for 2.5 hours. The mixture was filtered and rinsed with ethyl acetate, concentrated under reduced pressure and the resulting crude was purified by flash chromatography eluting with hexanes:isopropyl alcohol (3:2) to give the title compound (0.80 g, 55%) as a yellowish solid.

Workup

  1. filtrationThe mixture was filtered
  2. washrinsed with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting crude was purified by flash chromatography
  5. washeluting with hexanes:isopropyl alcohol (3:2)

Sources & evidence

ORD record
ord-38617bbb005946b4956f0132b715cab6
Source dataset
uspto-grants-2012_09
Patent number
US08258122B2

Reaction notes

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