Methanol → HCID 68764043, compound

HRID 79564Notes

Reaction equation

HRID 79564 reaction equation
[C:1]1([C:7]2[C:8]([N:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]3)=[C:9]3[CH:15]=[CH:14][N:13](S(C4C=CC=CC=4)(=O)=O)[C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.CO.[Li+].[OH-]>O>[C:1]1([C:7]2[C:8]([N:25]3[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:30]3)=[C:9]3[CH:15]=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68765500tert-Butyl 4-(5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 68764043HCID 68764043, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl 4-(5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (1.10 g, 2.12 mmol) was placed in 1:1 THF:MeOH (20 mL). LiOH (3.54 mL, 10.6 mmol) was then added, and the reaction was heated to 50° C. for 1 hour. The reaction was cooled to room temperature, poured into water, and extracted with DCM (3×50 mL). The combined organic fractions were dried, filtered, concentrated, and then purified by column chromatography (500:5 DCM:MeOH) to give tert-butyl 4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.40 g, 49.8% yield).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with DCM (3×50 mL)
  3. customThe combined organic fractions were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (500:5 DCM:MeOH)

Sources & evidence

ORD record
ord-a656d110436040da99fe7a10e8984bfc
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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