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

HRID 731059Notes

Reaction equation

HRID 731059 reaction equation
C[O:2][C:3](=[O:36])[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[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[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:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:36])=[O:2])=[CH:7][CH:8]=3)=[CH:20][CH:19]=2)[C:15]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[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 68815400HCID 68815400, compound

Product 1

HCID 11476726[4-(1,3-Dibenzyl-2-methyl-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-(1,3-dibenzyl-2-methyl-1H-indol-5-yl)-phenoxy]-acetic acid methyl ester (0.147 g, 0.309 mmol) was reacted with 1N KOH (0.62 ml) in THF/MeOH (3 ml/2 ml) to give the product (0.072 g, 0.156 mmol, 50%) as a tan solid, mp 180-183° C. 1H NMR (DMSO-d6), δ 2.35 (s, 3H), 4.10 (s, 2H), 4.66 (s, 2H), 5.42 (s, 2H), 6.94 (d, J=8.9 Hz, 2H), 6.99 (d, J=7.0 Hz, 2H), 7.09-7.13 (m, 1H), 7.20-7.30 (m, 8H), 7.39 (d, J=8.4 Hz, 1H), 7.49 (d, J=8.7 Hz, 2H), 7.58 (d, J=1.5 Hz, 1H), 13.00 (broad s, 1H); IR (solid) 3010, 2905, 1730, 1520, 1480, and 1240 cm−1; [ESI(+)], m/z 462 (M+H)+; Anal. Calcd. for C31H27NO3: C, 80.67; H, 5.90; N, 3.03; Found: C, 80.60; H, 5.79; N, 2.94.

Sources & evidence

ORD record
ord-318c447f4b444be7a72020cdd38e04c7
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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