Azobisisobutyronitrile → HCID 57925823, compound

HRID 1013452Notes

Reaction equation

HRID 1013452 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH3:11][P:12]([O:16]CC)[O:13][CH2:14][CH3:15].CC(N=NC(C#N)(C)C)(C#N)C.C[Si]([SiH]([Si](C)(C)C)[Si](C)(C)C)(C)C>C1(C)C=CC=CC=1>[CH2:14]([O:13][P:12]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1)([CH3:11])=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 85063Diethyl methylphosphoniteHCID 123134Tris(trimethylsilyl)silaneHCID 2389326-Bromonicotinic acid

Product 1

HCID 57925823HCID 57925823, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

6-Bromonicotinic acid (150 mg, 0.74 mmol) and diethyl methylphosphonite (1.21 g, 8.91 mmol) were dissolved in toluene and the solution was purged with argon for several minutes. The mixture was brought to reflux and a solution of AIBN (40 mg, 0.22 mmol) and tris trimethylsilylsilane (220 mg, 0.89 mmol) in toluene was added dropwise over 4 hours via syringe pump. The initiator was added via syringe pump over 4 hours. The resulting mixture was reluxed for 16 hours then it was concentrated in vacuo and purified directly by MPLC (0-50% EtOAc:Hex). MS: cal'd 230 (MH+), exp 230 (MH+).

Workup

  1. customthe solution was purged with argon for several minutes
  2. temperatureto reflux
  3. additionThe initiator was added via syringe pump over 4 hours
  4. concentrationit was concentrated in vacuo
  5. custompurified directly by MPLC (0-50% EtOAc:Hex)

Sources & evidence

ORD record
ord-8c82be76d3c0478fb8138dd56601e6dd
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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