Potassium Hydroxide → HCID 22032953, compound

HRID 1791429Notes

Reaction equation

HRID 1791429 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=[C:13]3[C:26](=[O:32])[C:27]([O:29]CC)=[O:28])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[K+]>C1COCC1.O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=[C:13]3[C:26](=[O:32])[C:27]([OH:29])=[O:28])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22032981HCID 22032981, compound

Product 1

HCID 22032953HCID 22032953, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

[5-(4-Acetylphenyl)-1-benzyl-1H-indol-3-yl](oxo)acetic acid was prepared from ethyl [5-(4-acetylphenyl)-1-benzyl-1H-indol-3-yl](oxo)acetate (0.225 g, 0.529 mmol), and potassium hydroxide (0.104 g, 1.85 mmol) in THF (7 mL) and water (7 mL) according to the procedure described in Step 4 of Example 5. After drying for 15 hours at 96° C., the title compound was obtained as a tan solid (0.166 g, 79%), mp: 213-214° C. (dec.). Mass spectrum (−APCI, [M−H]−) m/z 396; 1HNMR (400 MHz, DMSO-d6): δ 8.75 (s, 1H), 8.5 (d, 1H, J=1.7 Hz), 8.05 (d, 2H, J=8.3 Hz), 7.8 (d, 2H, J=8.3 Hz), 7.7 (d, 1H, J=8.8 Hz), 7.65 (dd, 1H, J=8.7 Hz and 1.6 Hz), 7.25-7.4 (m, 5H), 5.65 (s, 2H), and 2.6 ppm (s, 3H).

Workup

  1. customAfter drying for 15 hours at 96° C.

Sources & evidence

ORD record
ord-90ba35bbb5744071ba40ae18809bfa2a
Source dataset
uspto-grants-2006_07
Patent number
US07074817B2

Reaction notes

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