Methanol → Tert-butyl 4-(1H-pyrrolo[2,3-B]pyridin-3-YL)piperazine-1-carboxylate

HRID 641896Notes

Reaction equation

HRID 641896 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[C:12]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+].CO>O>[NH:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C:12]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)=[CH:11]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 592593311-Piperazinecarboxylic acid, 4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-, 1,1-dimethylethyl ester

Product 1

HCID 49758941Tert-butyl 4-(1H-pyrrolo[2,3-B]pyridin-3-YL)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Into a 50 mL round bottom flask purged and maintained with an inert atmosphere of nitrogen was placed tert-butyl 4-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)piperazine-1-carboxylate (400 mg, 0.90 mmol). To this was added NaOH (90 mg, 2.25 mmol). Addition of methanol (20 mL) was next. To the mixture was added H2O (8 mL). The resulting solution was allowed to react, with stirring, for 4 hours while the temperature was maintained at 90° C. in a bath of oil. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. A filtration was performed and the filter cake was washed with H2O. This resulted in 180 mg (66%) of tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperazine-1-carboxylate as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 1.40 (s, 9H), 2.96 (m, 4H), 3.56 (m, 4H), 6.73 (s, 1H), 6.97 (d, 1H), 7.88 (d, 1H), 8.22 (d, 1H), 8.97 (s, 1H). m/z 303 (M++1).

Workup

  1. customInto a 50 mL round bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customto react
  4. concentrationThe mixture was concentrated by evaporation under vacuum
  5. customa rotary evaporator
  6. filtrationA filtration
  7. washthe filter cake was washed with H2O
  8. customThis resulted in 180 mg (66%) of tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperazine-1-carboxylate as a light yellow solid

Sources & evidence

ORD record
ord-97c587ad20c744b2ad3aac01b349f2d5
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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