Sodium Hydroxide → HCID 67958067, compound

HRID 1529427Notes

Reaction equation

HRID 1529427 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16](S(C2C=CC(C)=CC=2)(=O)=O)[CH:15]=[C:14]3[C:30]([OH:32])=[O:31])[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[C:30]([OH:32])=[O:31])[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67960142HCID 67960142, compound

Product 1

HCID 67958067HCID 67958067, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-(6-isopropoxy-pyrazin-2-yl)-1-(toluene-4-sulfonyl)-1H-indole-3-carboxylic acid (450 mg, 0.99 mmol) in 1,4-dioxane (5 mL) was added of 10% aq. NaOH (5 mL) at RT and the reaction was heated at 90° C. for 1 h. The reaction was cooled to RT and washed with DCM (2×3 mL). The aqueous layer was neutralized with 1N HCl (4 mL) and was extracted with EtOAc (5 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give 5-(6-isopropoxypyrazin-2-yl)-1H-indole-3-carboxylic acid (35 mg, 12%) as a brown solid. MS (ESI, pos. ion) m/z: 298.1 (M+1).

Workup

  1. temperatureThe reaction was cooled to RT
  2. washwashed with DCM (2×3 mL)
  3. extractionwas extracted with EtOAc (5 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be7d006e4dbb4ebda7357514e7a18437
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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