HCID 12150668, compound → HCID 10111204, compound

HRID 2086150Notes

Reaction equation

HRID 2086150 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH3:27])[C:7]2[C:12]([CH:13]=1)=[C:11]([Cl:14])[C:10]([O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH:23]([CH3:25])[CH3:24])[CH:17]=1)=[C:9]([Cl:26])[CH:8]=2)=[O:4]>CO.[OH-].[K+]>[Cl:14][C:11]1[C:10]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH:23]([CH3:25])[CH3:24])[CH:17]=2)=[C:9]([Cl:26])[CH:8]=[C:7]2[C:12]=1[CH:13]=[C:5]([C:3]([OH:4])=[O:2])[N:6]2[CH3:27]

Participants

4

Reactant 1

HCID 12150668HCID 12150668, compound

Product 1

HCID 10111204HCID 10111204, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent2×

Procedure

To a solution of 4,6-dichloro-5-(4-hydroxy-3-isopropyl-phenoxy)-1-methyl-1H-indole-2-carboxylic acid methyl ester (32 mg, 0.078 mmol) in 50% aqueous MeOH (4 mL) was added potassium hydroxide (3N, 154 μL). The resulting solution was stirred for 19 hours at room temperature, diluted with potassium hydroxide (0.1N, 16 mL) and the solution was washed with EtOAc (3 times 10 mL). The aqueous solution was acidified with concentrated hydrochloric acid and then extracted with ethyl acetate (3 times 15 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated to afford the title compound (23 mg). 1H NMR (400 MHz, CD3OD) δ7.64 (s, 1H), 7.24 (s, 1H), 6.63 (d, 1H), 6.57 (d, 1H), 6.29-6.26 (dd, 1H), 4.03 (s, 3H), 3.22-3.15 (m, 1H), 1.11 (d, 6H). MS (APCI−) Calc: 393.0, Found: 392.2 (M−1).

Workup

  1. washthe solution was washed with EtOAc (3 times 10 mL)
  2. extractionextracted with ethyl acetate (3 times 15 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-06a7c72406fb4a94bad83fca740327db
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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