Sodium hydride → HCID 58289687, compound

HRID 1422541Notes

Reaction equation

HRID 1422541 reaction equation
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[C:5]([Cl:22])[C:6]([O:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:7][CH:8]=2)[N:3]=1.[CH:23]([C:26]1[CH:30]=[CH:29][NH:28][N:27]=1)([CH3:25])[CH3:24].[H-].[Na+]>CN1C(=O)CCC1>[Cl:12][C:10]1[C:9]2[C:4](=[C:5]([Cl:22])[C:6]([O:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:7][CH:8]=2)[N:3]=[C:2]([N:28]2[CH:29]=[CH:30][C:26]([CH:23]([CH3:25])[CH3:24])=[N:27]2)[CH:11]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 57909932HCID 57909932, compoundHCID 178439403HCID 178439403, compound

Product 1

HCID 58289687HCID 58289687, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To mixture of 2,4,8-trichloro-7-(2-morpholin-4-yl-ethoxy)-quinoline (0.34 g, 0.95 mmol) and 3-isopropyl-1H-pyrazole (0.63 g, 5.7 mmol) in NMP (3 ml) was added NaH (60% in mineral oil) (0.042 g, 1.05 mmol). The mixture was stirred at room temperature for over night and it monitored by LC-MS. The crude material was purified by pre-HPLC to afford 4,8-dichloro-2-(3-isopropyl-pyrazol-1-yl)-7-(2-morpholin-4-yl-ethoxy)-quinoline (0.204 g, 0.47 mmol).

Workup

  1. customThe crude material was purified by pre-HPLC

Sources & evidence

ORD record
ord-27e26657e37542e5aa22e99457cbd2ed
Source dataset
uspto-grants-2015_01
Patent number
US08927484B2

Reaction notes

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