Potassium Hydroxide → HCID 10163488, compound

HRID 2221216Notes

Reaction equation

HRID 2221216 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=3)=[CH:14][CH:15]=2)[C:10]([C:31](=[O:37])[C:32]([O:34]CC)=[O:33])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C1COCC1.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:18]=[C:19]([C:27]([F:28])([F:29])[F:30])[CH:20]=[C:21]([C:23]([F:26])([F:24])[F:25])[CH:22]=3)=[CH:14][CH:15]=2)[C:10]([C:31](=[O:37])[C:32]([OH:34])=[O:33])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22032954HCID 22032954, compound

Product 1

HCID 10163488HCID 10163488, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

{1-Benzyl-5-[3,5-bis(trifluoromethyl)phenyl]-1H-indol-3-yl}(oxo)acetic acid was prepared from ethyl {1-benzyl-5-[3,5-bis(trifluoromethyl)phenyl]-1H-indol-3-yl}(oxo)acetate (0.737 g, 1.42 mmol), potassium hydroxide (0.260 g, 4.63 mmol) in THF (9 mL) and water (9 mL) according to the procedure described in Step 4 of Example 5. Purification by crystallization from acetonitrile and drying at 88° C. furnished the title compound as a white solid (0.326 g, 47%), mp: 206-207° C. Mass spectrum (+APCI, [M+H]+) m/z 492; 1HNMR (400 MHz, DMSO-d6): δ 13.8-14.3 (br s, 1H), 8.75 (s, 1H), 8.5 (s, 1H), 8.25 (s, 2H), 8.1 (s, 1H), 7.75 (s, 2H), 7.25-7.35 (m, 5H), and 5.6 ppm(s, 2H). Elemental Analysis for C25H15F6NO3: Calculated: C, 61.11; H, 3.08; N, 2.85. Found: C, 60.91; H, 2.87; N, 2.83.

Workup

  1. customPurification
  2. customby crystallization from acetonitrile
  3. customdrying at 88° C.

Sources & evidence

ORD record
ord-b32411b9b7e94e74820ec3f0d75aba24
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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