Hexane → HCID 10158332, compound

HRID 2221223Notes

Reaction equation

HRID 2221223 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=2)[C:10]([C:25](=[O:31])[C:26]([O:28]CC)=[O:27])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].CCCCCC>C1COCC1.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=2)[C:10]([C:25](=[O:31])[C:26]([OH:28])=[O:27])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 14797Potassium HydroxideHCID 22032966HCID 22032966, compound

Product 1

HCID 10158332HCID 10158332, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

[1-Benzyl-7-(3-chloro-4-fluorophenyl)-1H-indol-3-yl](oxo)acetic acid was prepared from ethyl 2-[1-benzyl-7-(3-chloro-4-fluorophenyl)-1H-indol-3-yl]-2-oxoacetate (0.139 g, 0.319 mmol), and potassium hydroxide (0.076 g, 1.35 mmol) in THF (2.5 mL) and water (2.5 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. Drying for 12 hours at 82° C. yielded the title compound as a yellow solid (0.0836 g, 64%), mp: 153-156° C. Mass spectrum (−ESI, [M−H]−) m/z 406; 1HNMR (500 MHz, DMSO-d6): δ 13.8-14.2 (br s, 1H), 8.65 (s, 1H), 8.35 (m, 1H), 7.3-7.35 (m, 2H), 7.05-7.2 (m, 5H), 7.0 (s, 1H, J=7.1 Hz), 6.35 (d, 2H, J=6.9 Hz), 5.35 (d, 1H, J=16.6 Hz), and 5.15 ppm (d, 1H, J=16.6 Hz). Elemental Analysis for C23H15ClFNO3: Calculated: C, 67.74; H, 3.71; N, 3.43. Found: C, 67.53; H, 3.9; N, 3.3.

Workup

  1. customa solid was obtained
  2. customDrying for 12 hours at 82° C.

Sources & evidence

ORD record
ord-2b5dd283b3d2490bb2f41f0761ee3ae8
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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