Potassium Hydroxide → HCID 11442243, compound

HRID 731080Notes

Reaction equation

HRID 731080 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]=[CH:19][CH:18]=[C:17]3[C:13]=2[C:14]([CH3:34])=[C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:16]3[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:8][CH:7]=1.[OH-].[K+]>C1COCC1.CO>[CH2:21]([N:16]1[C:17]2[C: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]=[CH:19][CH:18]=2)[C:14]([CH3:34])=[C:15]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

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68814795HCID 68814795, compound

Product 1

HCID 11442243HCID 11442243, compound

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-3-methyl-2-phenyl-1H-indol-4-yl)-phenoxy]-acetic acid methyl ester (0.263 g, 0.570 mmol) was reacted with 1N KOH (1.1 ml) in THF/MeOH (3 ml/2 ml) to give the product (0.198 g, 0.442 mmol, 78%) as a white foam, mp 82-86° C. 1H NMR (DMSO-d6) δ 1.72 (s, 3H), 4.70 (s, 2H), 5.29 (m, 2H), 6.84 (d, J=7.2 Hz, 1H), 6.88 (d, J=7.3 Hz, 2H), 6.96 (d, J=8.6 Hz, 2H), 7.11 (t, J=7.5 Hz, 1H), 7.16 (t, J=7.0 Hz, 1H), 7.22 (t, J=7.0 Hz, 2H), 7.31-7.34 (m, 5H), 7.40 (t, J=7.0 Hz, 1H), 7.45 (t, J=6.7 Hz, 2H); IR (solid) 3030, 2910, 1730, 1605, 1520, 1480, 1430, 1210, and 1180 cm−1; [ESI(+)], m/z 448 (M+H)+; Anal. Calcd. for C30H25NO3.0.33H2O: C, 80.51; H, 5.63; N, 3.13; Found: C, 79.30; H, 5.78; N, 3.00.

Sources & evidence

ORD record
ord-388b76e25c9b4b42bf0f2c8907f0df52
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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