Potassium Hydroxide → HCID 11339826, compound

HRID 731073Notes

Reaction equation

HRID 731073 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:20]=[C:19]3[C:15]([C:16]([CH3:34])=[C:17]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:18]3[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[OH-].[K+]>>[CH2:21]([N:18]1[C:19]2[C:15](=[CH:14][CH:13]=[C:12]([C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:35])=[O:2])=[CH:7][CH:8]=3)[CH:20]=2)[C:16]([CH3:34])=[C:17]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 68814951HCID 68814951, compound

Product 1

HCID 11339826HCID 11339826, compound

Procedure

The desired product was prepared using a procedure similar to step 2 of example 4. Thus, [4-(1-benzyl-3-methyl-2-phenyl-1H-indol-6-yl)-phenoxy]-acetic acid methyl ester (0.299 g, 0.648 mmol) was reacted with 1N KOH (1.3 ml) to give the product (0.231 g, 0.511 mmol, 79%) as a white solid, mp 202-205° C. 1H NMR (DMSO-d6) δ 2.23 (s, 3H), 4.68 (s, 2H), 5.39 (s, 2H), 6.86 (d, J=7.2 Hz, 2H), 6.96 (d, J=8.9 Hz, 2H), 7.13 (t, J=7.2 Hz, 1H), 7.18 (t, J=7.0 Hz, 2H), 7.34 (dd, J=1.4, 8.3 Hz, 1H), 7.39-7.44 (m, 3H), 7.49 (t, J=7.0 Hz, 2H), 7.56-7.61 (m, 4H); IR (solid) 3280, 2905, 1760, 1720, 1605, 1520, 1480, 1440, and 1240 cm1; [ESI(+)], m/z 448 (M+H)+; Anal. Calcd. for C30H25NO3.0.25H2O: C, 79.71; H, 5.57; N, 3.10; Found: C, 79.79; H, 5.66; N, 3.05.

Sources & evidence

ORD record
ord-d354d3ea93684737ae9b81eb9f3a753f
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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