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

HRID 731066Notes

Reaction equation

HRID 731066 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]([CH3:21])[C:16]([CH3:22])=[C:15]3[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:8][CH:7]=1.[OH-].[K+]>C1COCC1.CO>[CH2:23]([C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[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:13]=2)[N:17]([CH3:21])[C:16]=1[CH3:22])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68814817HCID 68814817, compound

Product 1

HCID 11222886[4-(3-Benzyl-1,2-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-(3-benzyl-1,2-dimethyl-1H-indol-5-yl)-phenoxy]-acetic acid methyl ester (0.151 g, 0.378 mmol) was reacted with 1N KOH (0.8 ml) in THF/MeOH (3 ml/2 ml) to give the product (0.068 g, 0.176 mmol, 47%) as a yellow solid, mp 204-207° C. 1H NMR (DMSO-d6) δ 2.40 (s, 3H), 3.67 (s, 3H), 4.06 (s, 2H), 4.67 (s, 2H), 6.94 (d, J=8.9 Hz, 2H), 7.08-7.12 (m, 1H), 7.19-7.24 (m, 4H), 7.28 (dd, J=1.7, 8.6 Hz, 1H), 7.39 (d, J=8.4 Hz, 1H), 7.50 (d, J=8.7 Hz, 2H), 7.56 (d, J=1.4 Hz, 1H); IR (solid) 3020, 2880, 1740, 1710, 1510, 1480, and 1230 cm−1; [ESI(+)], m/z 386 (M+H)+; Anal. Calcd. for C25H23NO3.0.3H2O: C, 76.82; H, 6.17; N, 3.58; Found: C, 76.66; H, 6.00; N, 3.46.

Sources & evidence

ORD record
ord-bdc2a97065044fa0af7105f4387ca21c
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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