Water → (2,5-Di-pyridin-3-yl-pyrrol-1-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester

HRID 1265293Notes

Reaction equation

HRID 1265293 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=O)[CH2:8][CH2:9][C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=O)[CH:2]=1.[CH3:19][Si:20]([CH3:29])([CH3:28])[CH2:21][CH2:22][O:23][C:24]([NH:26][NH2:27])=[O:25].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:19][Si:20]([CH3:29])([CH3:28])[CH2:21][CH2:22][O:23][C:24](=[O:25])[NH:26][N:27]1[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:8][CH:9]=[C:10]1[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 10241327Hydrazinecarboxylic acid 2-trimethylsilanyl-ethyl esterHCID 186154701,4-Di-pyridin-3-yl-butane-1,4-dione

Product 1

HCID 69946665(2,5-Di-pyridin-3-yl-pyrrol-1-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1,4-di-Pyridin-3-yl-butane-1,4-dione (1 g, 4.2 mmol) in toluene (40 mL) is treated with hydrazinecarboxylic acid 2-trimethylsilanyl-ethyl ester (888 mg, 5.0 mmol) and p-toluenesulfonic acid (30 mg). The reaction vessel is fitted with a Dean Stark trap, and the resulting solution is heated to reflux, with azeotropic removal of water until no starting materials are detected by TLC. The solution is cooled to rt, and washed with water. The organic layer is dried over Na2SO4, filtered and concentrated to afford (2,5-di-pyridin-3-yl-pyrrol-1-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester, which is not purified further.

Workup

  1. customThe reaction vessel is fitted with a Dean Stark trap
  2. temperaturethe resulting solution is heated
  3. washwashed with water
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-463986574b82466bab26b005e5b12c7a
Source dataset
uspto-grants-2003_04
Patent number
US06545108B1

Reaction notes

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