Potassium Hydroxide → [4-(1-Benzyl-2,3-dimethyl-1H-indol-5-yl)-phenoxy]-acetic acid

HRID 731039Notes

Reaction equation

HRID 731039 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]([CH3:28])=[C:15]3[CH3:29])=[CH:8][CH:7]=1.[OH-].[K+]>C1COCC1.CO>[CH2:21]([N:17]1[C:18]2[C:14](=[CH:13][C:12]([C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][C:3]([OH:30])=[O:2])=[CH:11][CH:10]=3)=[CH:20][CH:19]=2)[C:15]([CH3:29])=[C:16]1[CH3:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68814065HCID 68814065, compound

Product 1

HCID 11395029[4-(1-Benzyl-2,3-dimethyl-1H-indol-5-yl)-phenoxy]-acetic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The desired product was prepared using a procedure similar to step 2 of example 4. Thus, [4-(1-benzyl-2,3-dimethyl-1H-indol-5-yl)-phenoxy]-acetic acid methyl ester (0.230 g, 0.576 mmol) was reacted with 1N KOH (1.2 ml) in THF/MeOH (6 ml/4 ml) to give the product (0.139 g, 0.361 mmol, 63%) as an off-white solid, mp 203-206° C. 1H NMR (DMSO-d6) δ 2.24 (s, 3H), 2.27 (s, 3H), 4.68 (s, 2H), 5.38 (s, 2H), 6.95-6.99 (m, 4H), 7.20 (t, J=7.2 Hz, 1H), 7.25-7.29 (m, 3H), 7.37 (d, J=8.6 Hz, 1H), 7.58 (d, J=8.7 Hz, 2H), 7.62 (s, 1H), 13.00 (broad s, 1H); IR (solid) 3030, 2910, 1740, 1710, 1605, 1520, 1480, and 1240 cm−1; [ESI(−)], m/z 384 (M−H)—; Anal. Calcd. for C25H23NO3: C, 77.90; H, 6.01; N, 3.63; Found: C, 77.87; H, 5.99; N, 3.64.

Sources & evidence

ORD record
ord-ed9f620db2ec4ff8be524998af36c213
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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