Potassium Hydroxide → HCID 10382556, compound

HRID 2086147Notes

Reaction equation

HRID 2086147 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([CH3:15])[C:11]([O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH:24]([CH3:26])[CH3:25])[CH:18]=1)=[C:10]([CH3:27])[CH:9]=2)=[O:5])C.[OH-].[K+]>CO.O.O>[OH:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:11]2[C:12]([CH3:15])=[C:13]3[C:8](=[CH:9][C:10]=2[CH3:27])[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]3)=[CH:18][C:19]=1[CH:24]([CH3:26])[CH3:25]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 12150663HCID 12150663, compound

Product 1

HCID 10382556HCID 10382556, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 5-(4-hydroxy-3-isopropyl-phenoxy)-4,6-dimethyl-1H-indole-2-carboxylic acid ethyl ester (60 mg, 0.16 mmol) in methanol/water (1:1, 3.2 mL) at room temperature was added 3N potassium hydroxide (324 μL). After stirring at room temperature for 2 hours, the mixture was diluted with water (10 mL) and washed with ethyl acetate. The aqueous solution was acidified with 1 M hydrochloric acid and then extracted with ethyl acetate (3 times 25 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford the title compound (30 mg) as a solid. 1H NMR (400 MHz, CD3OD) δ11.07 (s, 1H), 7.16 (s, 2H), 6.62 (d, 1H), 6.57 (d, 1H), 6.25-6.22 (dd, 1H), 3.24-3.19 (m, 1H), 2.27 (s, 3H), 2.17 (s, 3H), 1.12 (d, 6H). MS (APCI−) Calc: 339.1, Found: 338.2 (M−1).

Workup

  1. washwashed with ethyl acetate
  2. extractionextracted with ethyl acetate (3 times 25 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7cda59e7b2af47bbbfb8de84152d0eeb
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

Loading…