Sodium hydride → HCID 10324057, compound

HRID 859005Notes

Reaction equation

HRID 859005 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][N:26]=[CH:27]2)=[CH:22][CH:21]=1.[H-].[Na+]>CN(C=O)C>[CH: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][N:26]=[CH: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][N:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 4597677-IsoquinolinolHCID 21865297HCID 21865297, compound

Product 1

HCID 10324057HCID 10324057, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared analogous to the procedure used to prepare Example 48, using 3,6-dichloro-4-(4-trifluoromethyl-phenyl)-pyridazine, (Example 45(d)), (443 mg, 1.5 mmol), 7-hydroxyisoquinoline (444 mg, 3.1 mmol, Lancaster) and NaH (151 mg, 3.8 mmol, 60% suspension in mineral oil, Aldrich) in DMF (10 mL). Purification by flash silica gel chromatography with 2M NH3 in MeOH/CH2Cl2 (0:1→1:24) as eluant gave the title compound as a tan amorphous solid. Mp: 82–86° C. MS (ESI, pos ion.) m/z: 511 (M+1).

Workup

  1. customThe title compound was prepared analogous to the procedure
  2. customto prepare Example 48
  3. customPurification by flash silica gel chromatography with 2M NH3 in MeOH/CH2Cl2 (0:1→1:24) as eluant

Sources & evidence

ORD record
ord-5b83ab4cbe4d4b51baf28c429293625d
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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