Potassium Hydroxide → HCID 10294846, compound

HRID 2221213Notes

Reaction equation

HRID 2221213 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=3)=[CH:14][CH:15]=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+]>C1COCC1.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=3)=[CH:14][CH:15]=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

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86588617HCID 86588617, compound

Product 1

HCID 10294846HCID 10294846, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

[1-Benzyl-5-(3-chloro-4-fluorophenyl)-1H-indol-3-yl](oxo)acetic acid was prepared from ethyl [1-benzyl-5-(3-chloro-4-fluorophenyl)-1H-indol-3-yl](oxo)acetate (0.540 g, 1.24 mmol), and potassium hydroxide (0.218 g, 3.89 mmol) in THF (6 mL) and water (6 mL) according to the procedure described in Step 4 of Example 5. Purification by crystallization from methylene chloride/hexane and drying at 85° C. furnished the title compound as a white solid (0.319 g, 63%), mp: 145-146° C. (dec.). Mass spectrum (+APCI, [M+H]+) m/z 408; 1HNMR (400 MHz, DMSO-d6): δ 13.8-14.3 (br s, 1H), 8.75 (s, 1H), 8.4 (d, 1H, J=1.7 Hz), 7.8 (dd, 1H, J=7.2 Hz and 2.3 Hz), 7.65-7.7 (m, 2H), 7.6 (dd, 1H, J=8.5 Hz and 2.0 Hz), 7.5 (t, 1H, J=8.9 Hz), 7.25-7.35 (m, 5H), and 5.6 ppm (s, 2H). Elemental Analysis for C23H15ClFNO3.H2O: Calculated: C, 67.44; H, 3.74; N, 3.42. Found: C, 67.24; H, 3.6; N, 3.36.

Workup

  1. customPurification
  2. customby crystallization from methylene chloride/hexane
  3. customdrying at 85° C.

Sources & evidence

ORD record
ord-a2d0c8ff0e274e37ac48913167550224
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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