HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Potassium Hydroxide → 3-(2-tert-butoxy-6-chloropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 68339
Notes
Print preview

Reaction equation

HRID 68339 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14](S(C3C=CC=CC=3)(=O)=O)[CH:13]=2)[CH:9]=[C:8]([Cl:30])[N:7]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C.O>[C:1]([O:5][C:6]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH:9]=[C:8]([Cl:30])[N:7]=1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 874015973-(2-tert-butoxy-6-chloropyridin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 874023053-(2-tert-butoxy-6-chloropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of EXAMPLE 34B (2.15 g, 4.87 mmol) in 60 mL ethanol/water (5:1) was added powdered potassium hydroxide (1.09 g, 19.46 mmol). The suspension was heated at 50° C. for 3 hours, at which time the reaction was homogeneous. The solvent was removed and the crude material was dissolved in ethyl acetate, washed with water, and brine, dried over magnesium sulfate, filtered and concentrated. The crude material was purified by flash chromatography (Analogix 280, gradient elution, 20-100% ethyl acetate/hexane) to give the title compound. MS (ESI) m/e 301.9 (M+H)+.

Workup

  1. customThe solvent was removed
  2. dissolutionthe crude material was dissolved in ethyl acetate
  3. washwashed with water, and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography (Analogix 280, gradient elution, 20-100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e26e5c2d5e9945d599fa9d8e7796edaa
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822446B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes