Sodium hydride → 1-[(3,5-dichloropyridin-4-yl)methyl]-6-methoxy-4-phenylphthalazine

HRID 2297408Notes

Reaction equation

HRID 2297408 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].[H-].[Na+].Cl[C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:15][N:14]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH2:8][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[C:16]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:15][N:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 109538273,5-Dichloro-4-methylpyridineHCID 18381653HCID 18381653, compound

Product 1

HCID 99525921-[(3,5-dichloropyridin-4-yl)methyl]-6-methoxy-4-phenylphthalazineYield 47.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Operating as described in example 5 starting from 3,5-dichloro-4-methyl-pyridine (0.45 g, 2.81 mmoles) in dry DMF (10 ml), 60% NaH (67 mg, 2.81 mmoles) and 1-chloro-6-methoxy-4-phenyl-phthalazine (0.38 g, 1.4 mmoles), prepared as described in example 14, in DMF (10 ml), 0.26 g of the title compound were obtained (yield: 47.3%). m.p.: 206-208° C.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-866d36d6e14b43c48f484c8ee8c5bed3
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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