Sodium hydride → HCID 21717292, compound

HRID 1386333Notes

Reaction equation

HRID 1386333 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[H-].[Na+].[Cl:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH2:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][N:16]=1>CN(C=O)C>[ClH:14].[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH:5]2[C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH2:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6111935-Bromo-2-oxindoleHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline

Product 1

HCID 21717292HCID 21717292, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using an analogous procedure to that described in Example 50, 5-bromooxindole (318 mg, 1.5 mmol), (prepared according to J. Am. Chem. Soc. 1975, 67, 1656), was treated with sodium hydride (60 mg, 1.5 mmol) in DMF (4 ml) and 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (169 mg, 0.5 mmol), (prepared as described for the starting material in Example 5), to give 4-(5-bromooxindol-3-yl)-6-methoxy-7-(3-morpholinopropoxy)quinazoline hydrochloride (108 mg, 35%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-b98d5a685792405da8f4a3aaf795298b
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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