Methanol → tert-Butyl 4-(5-(3-fluorophenyl)-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 79526Notes

Reaction equation

HRID 79526 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([N:26]3[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]3)=[C:10]3[CH:16]=[CH:15][N:14](S(C4C=CC=CC=4)(=O)=O)[C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C1COCC1.CO.[Li+].[OH-]>O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([N:26]3[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]3)=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 687621981-Piperazinecarboxylic acid, 4-[5-(3-fluorophenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-, 1,1-dimethylethyl ester

Product 1

HCID 68762149tert-Butyl 4-(5-(3-fluorophenyl)-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazine-1-carboxylateYield 92.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl 4-(5-(3-fluorophenyl)-1-(phenyl sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.220 g, 0.410 mmol) was placed in 1:1 THF:MeOH (6 mL). 3M LiOH (0.683 mL, 2.05 mmol) was then added, and the reaction was stirred at 50° C. for 1 hour. The reaction was then cooled, added to water and extracted with DCM. The organic fractions were dried, filtered and concentrated to give the crude product tert-butyl 4-(5-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.150 g, 92.29% yield), which was used without further purification.

Workup

  1. temperatureThe reaction was then cooled
  2. extractionextracted with DCM
  3. customThe organic fractions were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c2ad9115341940e8a9d885fe09601dba
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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