Methanol → HCID 68762312, compound

HRID 79596Notes

Reaction equation

HRID 79596 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([N:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)=[C:10]2[CH:16]=[CH:15][N:14](S(C3C=CC=CC=3)(=O)=O)[C:11]2=[N:12][CH:13]=1.C1COCC1.CO.[Li+].[OH-]>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([N:26]2[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]2)=[C:10]2[CH:16]=[CH:15][NH:14][C:11]2=[N:12][CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68761346tert-butyl 4-(5-(2-fluorophenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 68762312HCID 68762312, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl 4-(5-(2-fluorophenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.100 g, 0.186 mmol) was placed in 1:1 THF:MeOH (6 mL). LiOH (0.621 mL, 1.86 mmol) was then added, and the reaction was stirred at 50° C. for 1 hour. The reaction was then poured into water and extracted into DCM. The organic fractions were combined, dried, filtered and concentrated to give the crude product tert-butyl 4-(5-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.066 g, 89.3% yield) that was used without further purification.

Workup

  1. extractionextracted into DCM
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8727bce343f94823b78666f90e2f36f1
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

Loading…