Potassium Hydroxide → HCID 11751226, compound

HRID 731115Notes

Reaction equation

HRID 731115 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:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[C:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:15]3[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:8][CH:7]=1.[OH-].[K+]>C1COCC1.CO>[CH2:28]([C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[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:13]=2)[N:17]([CH3:21])[C:16]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68814776HCID 68814776, compound

Product 1

HCID 11751226HCID 11751226, 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-(3-benzyl-1-methyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetic acid methyl ester (0.139 g, 0.301 mmol) was reacted with 1N KOH (0.6 ml) in THF/MeOH (3 ml/2 ml) to give the product (0.075 g, 0.168 mmol, 56%) as a white solid, mp 179-181° C. 1H NMR (DMSO-d6) δ 3.63 (s, 3H), 4.05 (s, 2H), 4.69 (s, 2H), 6.97 (d, J=8.9 Hz, 2H), 7.08-7.12 (m, 3H), 7.19 (t, J=7.6 Hz, 2H), 7.43 (dd, J=1.5, 8.4 Hz, 1H), 7.46-7.58 (m, 9H); IR (solid) 3020, 2910, 1730, 1705, 1605, 1510, 1480, 1430, 1370, 1270, and 1230 cm−1; [ESI(+)], m/z 448 (M+H)+; Anal. Calcd. for C30H25NO3: C, 80.51; H, 5.63; N, 3.13; Found: C, 80.15; H, 5.62; N, 3.11.

Sources & evidence

ORD record
ord-3a281b605eb646f9bea955ab6e72845b
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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