Sodium hydride → HCID 9927063, compound

HRID 2268829Notes

Reaction equation

HRID 2268829 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)[CH:16]=[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)[CH:16]=[N:15][N:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 109538273,5-Dichloro-4-methylpyridineHCID 183816081-Chloro-6-methoxyphthalazine

Product 1

HCID 9927063HCID 9927063, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3,5-dichloro-4-methyl-pyridine (11.32 g, 70 mmoles) in dry DMF (100 ml) was stirred under N2 at room temperature, then added with 60% NaH in oil (2.8 g, 70 mmoles). After 1 hour at room temperature a solution of 1-chloro-6-methoxy-phthalazine (6.8 g, 35 mmoles), prepared as described in example 4, in DMF (250 ml) was added. The mixture was left at room temperature for 20 hours, then poured into water/ice (pH≅8) and extracted more times with CH2Cl2. The organic phases were washed with water, anhydrified and brought to dryness to give a solid which was triturated in isopropyl ether (100 ml) and filtered. The mother liquors were dried and the residue flash chromatographed with ethyl acetate to give 8.9 g of the title compound (yield: 79.5%). m.p.: 173-175° C. 1H-NMR (CDCl3) δ: 9.32(s,1H); 8.50(s,2H); 8.11(d,1H,J=9.0 Hz); 7.56(dd,1H); 7.20(d,1H,J=2.6 Hz); 4.90(s,2H); 4.00(s,3H).

Workup

  1. customprepared
  2. additionwas added
  3. extractionextracted more times with CH2Cl2
  4. washThe organic phases were washed with water
  5. customto give a solid which
  6. customwas triturated in isopropyl ether (100 ml)
  7. filtrationfiltered
  8. customThe mother liquors were dried
  9. customthe residue flash chromatographed with ethyl acetate

Sources & evidence

ORD record
ord-3ec9fb3027bd46e08d6e4222a05a299e
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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