Sodium hydride → HCID 10412181, compound

HRID 1823219Notes

Reaction equation

HRID 1823219 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH3:14])[CH:6]=1.BrC[CH2:18][C:19]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[N:21]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[N:20]=1.[H-].[Na+]>CN(C=O)C>[CH3:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([N:21]2[C:22]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[CH:23][C:19]([CH2:18][CH:4]([C:5]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[N:7]([CH3:14])[CH:6]=3)[C:3]([OH:2])=[O:15])=[N:20]2)=[CH:36][CH:35]=1.[CH3:1][O:2][C:3](=[O:15])[CH:4]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH3:14])[CH:6]=1)[CH2:18][C:19]1[CH:23]=[C:22]([C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)[N:21]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[N:20]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 11106438Methyl 2-(1-methyl-1H-indol-3-yl)acetateHCID 688750633-bromoethyl-1-(4-methoxy-phenyl)-5-p-tolyl-1H-pyrazole

Product 2

HCID 10412181HCID 10412181, compoundHCID 688780353-[1-(4-methoxy-phenyl)-5-p-tolyl-1H-pyrazol-3-yl]-2-(1-methyl-1H-indol-3-yl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[1-(4-Methoxy-phenyl)-5-β-tolyl-1-H-pyrazol-3-yl]-2-(1-methyl-1H-indol-3-yl)-propionic acid. The title compound was prepared by Method 2 from (1-methyl-1H-indol-3-yl)-acetic acid methyl ester (0.10 g, 0.49 mmol), 3-bromoethyl-1-(4-methoxy-phenyl)-5-p-tolyl-1H-pyrazole (89 mg, 0.25 mmol), sodium hydride (19 mg, 0.49 mmol) and DMF (4.0 mL), giving 3-[1-(4-methoxy-phenyl)-5-p-tolyl-1H-pyrazol-3-yl]-2-(1-methyl-1H-indol-3-yl)-propionic acid methyl ester, which was not isolated. The ester was converted to the acid in situ by adding 2.5 mL (4.9 mmol) LiOH solution giving 57 mg (49%) of 3-[1-(4-methoxy-phenyl)-5-p-tolyl-1H-pyrazol-3-yl]-2-(1-methyl-1H-indol-3-yl)-propionic acid. HPLC: Rt=3.23 (Method B). MS (ES+): mass calculated for C29H27N3O3, 465.21; m/z found 466.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 12.15 (brs, 1H), 7.64 (d, J=7.9 Hz, 1H), 7.40 (d, J=8.2 Hz, 1H), 7.32 (s, 1H), 7.17-7.10 (m, 5H), 7.05-7.03 (m, 3H), 6.93 (d, J=8.9 Hz, 2H), 6.38 (s, 1H), 4.22 (dd, J=9.1, 5.9 Hz, 1H), 3.76 (s, 6H), 3.44 (dd, J=14.7, 9.2 Hz, 1H), 3.04 (dd, J=5.9, 14.7 Hz, 1H), 2.27 (s, 3H).

Sources & evidence

ORD record
ord-d10bd8eaf0c14f75936f9896ae9a1610
Source dataset
uspto-grants-2006_05
Patent number
US07037931B2

Reaction notes

Loading…