Diisopropylethylamine → 2-(4-Chlorophenyl)-5-(1H-imidazol-1-yl)-4-[4-(4-pyridinyl)phenoxy]-3(2H)-pyridazinone

HRID 2252290Notes

Reaction equation

HRID 2252290 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[C:10](=[O:27])[N:11]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[N:12]=[CH:13][C:14]=2[N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:4][CH:3]=1.C[Sn](C)(C)[C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1.C(N(C(C)C)C(C)C)C>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([N:11]2[C:10](=[O:27])[C:9]([O:8][C:5]3[CH:6]=[CH:7][C:2]([C:30]4[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=4)=[CH:3][CH:4]=3)=[C:14]([N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)[CH:13]=[N:12]2)=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 11128458Pyridine, 4-(trimethylstannyl)-HCID 585853834-(4-bromophenyl)oxy-2-(4-chlorophenyl)-5-(1H-imidazol-1-yl)-3(2H)-pyridazinone

Product 1

HCID 585852262-(4-Chlorophenyl)-5-(1H-imidazol-1-yl)-4-[4-(4-pyridinyl)phenoxy]-3(2H)-pyridazinone

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

1.5 mmol of 4-(4-bromophenyl)oxy-2-(4-chlorophenyl)-5-(1H-imidazol-1-yl)-3(2H)-pyridazinone, 2.1 mmol of 4-trimethylstannylpyridine, 0.1 mmol of bis(triphenyl-phosphine)palladium dichloride and 1.3 mmol of ethyldiisopropylamine in 5 ml of dimethylformamide are heated at 100° C. for 5 hours. The solvent is removed in a rotary evaporator, and the residue is purified by chromatography on silica gel (elution with ethyl, acetate/methanol mixtures). 0.3 g (45% of theory) is obtained of m.p. 188° C.

Workup

  1. customThe solvent is removed in a rotary evaporator
  2. customthe residue is purified by chromatography on silica gel (elution with ethyl, acetate/methanol mixtures)
  3. custom0.3 g (45% of theory) is obtained of m.p. 188° C.

Sources & evidence

ORD record
ord-9cc9fdcaf0964557b71979175a6485b3
Source dataset
uspto-grants-2008_01
Patent number
US07320977B2

Reaction notes

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