Hexane → HCID 10163714, compound

HRID 2221226Notes

Reaction equation

HRID 2221226 reaction equation
[C:1]([C:5]1[CH:38]=[CH:37][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=4)=[CH:16][CH:17]=3)[C:12]([C:30](=[O:36])[C:31]([O:33]CC)=[O:32])=[CH:11]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].CCCCCC>C1COCC1.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]([F:27])([F:28])[F:29])=[CH:21][CH:20]=4)=[CH:16][CH:17]=3)[C:12]([C:30](=[O:36])[C:31]([OH:33])=[O:32])=[CH:11]2)=[CH:37][CH:38]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8058HexaneHCID 14797Potassium HydroxideHCID 69248326HCID 69248326, compound

Product 1

HCID 10163714HCID 10163714, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

{1-[4-(tert-Butyl)benzyl]-5-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetic acid was prepared from ethyl {1-[4-(tert-butyl)benzyl]-5-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetate (1.72 g, 3.29 mmol), and potassium hydroxide (0.614 g, 10.9 mmol) in THF (20 mL) and water (20 mL) following the procedure described in Step 4 of Example 5. Following work-up, and trituration of the residue with hexane, a solid was obtained. Crystallization from methylene chloride/hexane and drying for 10 hours at 82° C. yielded the title compound as a yellow solid (1.12 g, 69%), mp: 158-160° C. Mass spectrum (−ESI, [M−H]−) m/z 494; 1HNMR (500 MHz, DMSO-d6): δ 13.8-14.1 (br s, 1H), 8.7 (s, 1H), 8.4 (d, 1H, J=1.4 Hz), 7.75 (d, 2H, J=8.7 Hz), 7.7 (d, 1H, J=8.7 Hz), 7.6 (dd, 1H, J=8.6 Hz and 1.7 Hz), 7.45 (d, 2H, J=8.2 Hz), 7.35 (d, 2H, J=8.4 Hz), 7.25 (d, 2H, J=8.4 Hz), 5.6 (s, 2H), and 1.2 ppm (s, 9H). Elemental Analysis for C28H24F3NO4: Calculated: C, 67.87; H, 4.88; N, 2.83. Found: C, 67.69; H, 4.83; N, 2.52.

Workup

  1. customa solid was obtained
  2. customCrystallization from methylene chloride/hexane
  3. customdrying for 10 hours at 82° C.

Sources & evidence

ORD record
ord-21b973cb724c4c5ebae3178eb45e118f
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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