3,6-Dichloropyridazine → 3-Iodo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine

HRID 548816Notes

Reaction equation

HRID 548816 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][OH:14].Cl[C:16]1[N:17]=[N:18][C:19]([I:22])=[CH:20][CH:21]=1.ClC1N=NC(Cl)=CC=1>>[I:22][C:19]1[N:18]=[N:17][C:16]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 673313,6-DichloropyridazineHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanolHCID 154188393-Chloro-6-iodopyridazine

Product 1

HCID 866308943-Iodo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazineYield 81%

Procedure

As described for example 1, (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (10.0 g, 53 mmol) was converted using 3-chloro-6-iodopyridazine (Goodman, A. J.; Stanforth, S. P.; Tarbit, B. Tetrahedron 1999, 55, 15067) instead of 3,6-dichloropyridazine to the title compound (16.9 g, 81%) which was contaminated with ca. 20% of 3-chloro-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine. The product was obtained as an off white solid. MS: m/e=394.0 [M+H]+.

Sources & evidence

ORD record
ord-07a34e480e6a4df29fc721f2a66fdd31
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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