Potassium Hydroxide → HCID 10224110, compound

HRID 2221207Notes

Reaction equation

HRID 2221207 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH:13]=[CH:14][CH:15]=2)[C:10]([C:27](=[O:33])[C:28]([O:30]CC)=[O:29])=[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](=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=3)[CH:13]=[CH:14][CH:15]=2)[C:10]([C:27](=[O:33])[C:28]([OH:30])=[O:29])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86588616HCID 86588616, compound

Product 1

HCID 10224110HCID 10224110, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-{1-Benzyl-4-[4-(trifluoromethyl)phenyl]-1H-indol-3-yl}-2-oxoacetic acid was prepared from ethyl {1-benzyl-4-[4-(trifluoromethyl)phenyl]-1H-indol-3-yl}(oxo)acetate (0.064 g, 0.142 mmol), and potassium hydroxide (0.0471 g, 0.839 mmol) in THF (2.5 mL) and water (2.5 mL) according to the procedure described in Step 4 of Example 5. The title compound was obtained as a light yellow solid (0.0497 g, 89%), mp: 183-184° C. Mass spectrum (+APCI, [M+H]+) m/z 424; 1HNMR (400 MHz, DMSO-d6): δ 13.5-14.0 (br s, 1H), 8.65 (s, 1H), 7.65-7.7 (m, 3H), 7.25-7.45 (m, 8H), 7.2 (dd, 1H, J=7.3 Hz and 0.73 Hz), and 5.65 ppm (s, 2H). Elemental Analysis for C24H16F3NO3.0.20 H2O: Calculated: C, 67.51; H, 3.87; N, 3.28. Found: C, 67.54; H, 3.56; N, 3.17.

Sources & evidence

ORD record
ord-98174df5a7684f2eaf35b6b3956d33b0
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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