p-Toluenesulfonic acid → 1-Piperazinecarboxylic acid, 4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-, 1,1-dimethylethyl ester

HRID 641895Notes

Reaction equation

HRID 641895 reaction equation
C(O[C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:5]=1)=O.[N:22]1([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:16]1([S:13]([N:6]2[C:7]3=[N:8][CH:9]=[CH:10][CH:11]=[C:12]3[C:4]([N:25]3[CH2:24][CH2:23][N:22]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:27][CH2:26]3)=[CH:5]2)(=[O:15])=[O:14])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 497589081H-Pyrrolo[2,3-B]pyridin-3-OL, 1-(phenylsulfonyl)-, 3-formate

Product 1

HCID 592593311-Piperazinecarboxylic acid, 4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Into a 150 mL sealed tube was placed 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl formate (1.5 g, 4.97 mmol). To this was added tert-butyl piperazine-1-carboxylate (9.24 g, 49.68 mmol). Addition of p-toluenesulfonic acid (171 mg, 0.99 mmol) was next. To the mixture was added toluene (70 mL). After nitrogen bubbled, the resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 120° C. in a bath of oil. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The residue was dissolved in 300 mL of ethyl acetate. The resulting mixture was washed 2 times with 150 mL of brine. The mixture was dried over Na2SO4. The residue was purified by eluting through a column with a 1:2 ethyl acetate/petroleum ether solvent system. This resulted in 420 mg (18%) of tert-butyl 4-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)piperazine-1-carboxylate as a yellow solid.

Workup

  1. customInto a 150 mL sealed tube
  2. customAfter nitrogen bubbled
  3. customto react
  4. concentrationThe mixture was concentrated by evaporation under vacuum
  5. customa rotary evaporator
  6. dissolutionThe residue was dissolved in 300 mL of ethyl acetate
  7. washThe resulting mixture was washed 2 times with 150 mL of brine
  8. dry with materialThe mixture was dried over Na2SO4
  9. customThe residue was purified
  10. washby eluting through a column with a 1:2 ethyl acetate/petroleum ether solvent system
  11. customThis resulted in 420 mg (18%) of tert-butyl 4-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)piperazine-1-carboxylate as a yellow solid

Sources & evidence

ORD record
ord-8d11c2346d7f46daae0418809a835b07
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

Loading…