Sodium hydride → HCID 11756064, compound

HRID 859004Notes

Reaction equation

HRID 859004 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.[OH:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][CH:26]=[N:27]2)=[CH:22][CH:21]=1.[H-].[Na+]>CN(C=O)C>[N:27]1[C:28]2[C:23](=[CH:22][CH:21]=[C:20]([O:19][C:5]3[N:4]=[N:3][C:2]([O:19][C:20]4[CH:29]=[C:28]5[C:23]([CH:24]=[CH:25][CH:26]=[N:27]5)=[CH:22][CH:21]=4)=[C:7]([C:8]4[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=4)[CH:6]=3)[CH:29]=2)[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21865297HCID 21865297, compoundHCID 1354268667-Hydroxyquinoline

Product 1

HCID 11756064HCID 11756064, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,6-dichloro-4-(4-trifluoromethyl-phenyl)-pyridazine, (Example 45(d)), (441 mg, 1.5 mmol) and 7-hydroxyquinoline (441 mg, 3.0 mmol, Acros) in DMF (10 mL) was added 60% NaH (150 mg, 3.8 mmol) and the mixture was heated at 80° C. for 14 h. The solvent was removed in vacuum, the residue was partitioned between EtOAc/H2O and the aqueous layer was extracted with EtOAc. The combined organic layers were evaporated onto SiO2 and purified by flash silica gel chromatography with EtOAc/hexanes (0:1→1:0) as eluant to give the title compound as an off-white amorphous solid. Mp: 158–162° C. MS (ESI, pos ion.) m/z: 511 (M+1).

Workup

  1. customThe solvent was removed in vacuum
  2. customthe residue was partitioned between EtOAc/H2O
  3. extractionthe aqueous layer was extracted with EtOAc
  4. customThe combined organic layers were evaporated onto SiO2
  5. custompurified by flash silica gel chromatography with EtOAc/hexanes (0:1→1:0) as eluant

Sources & evidence

ORD record
ord-3d96d2363a564d3381ea3a2f0ba7d397
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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