Imidazole → 5-(5-Chloro-thiophen-2-yl)-3-imidazol-1-ylmethyl-isoxazole

HRID 900253Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:13][C:14]1[CH:18]=[C:17]([C:19]2[S:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[O:16][N:15]=1>CC#N.C(Cl)Cl.[Br-].C([P+](C)(C)C)CCCCCCCCCCCCCCC>[Cl:24][C:21]1[S:20][C:19]([C:17]2[O:16][N:15]=[C:14]([CH2:13][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[CH:18]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of imidazole (34 mg) in MeCN (3 mL) was added K2CO3 (138 mg), n-hexadecyltrimethylphosphonium bromide (1 mg) and 3-bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole (139 mg). The mixture was stirred for 3 h at 70° C. After cooling to RT the reaction mixture was diluted with DCM (5 mL) and filtered. The filtrate was concentrated in vacuo to give crude 5-(5-Chloro-thiophen-2-yl)-3-imidazol-1-ylmethyl-isoxazole (153 mg) which was used in the next step without further purification.

Workup

temperatureAfter cooling to RT the reaction mixture
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-0242ba618bbd4ad4ba692f10e9dae8bc
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07358268B2

Reaction notes

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