Oxalyl chloride → 5-(2'-Methoxy-2-methylbiphenyl-4-YL)-3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

HRID 1950857Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[CH:17][C:16]=1[CH3:24].O[N:26]=[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:35][C:36]([F:39])([F:38])[F:37])[NH2:28].CCN(C(C)C)C(C)C>>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[O:23][N:28]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][C:36]([F:37])([F:38])[F:39])[N:26]=2)=[CH:17][C:16]=1[CH3:24]

Participants

Reactant 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 2794708N'-hydroxy-2-(trifluoromethoxy)benzenecarboximidamide

HCID 219477594-(2-Methoxyphenyl)-3-methylbenzoic acid

Product 1

HCID 252565655-(2'-Methoxy-2-methylbiphenyl-4-YL)-3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

Procedure

Oxalyl chloride (126 μL; 1.49 mmol; 3 eq.), Intermediate 26 (120 mg; 0.5 mmol; 1 eq.), Intermediate 2 (109 mg; 0.5 mmol, 1 eq.) and DIEA (256 μL; 1.49 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography (c-hexane/ethyl acetate, 95/5) afforded the title compound as a yellow oil.

Workup

customPurification by column chromatography (c-hexane/ethyl acetate, 95/5)

Sources & evidence

ORD record: ord-266f9a20ca364ff09e2539926917af49
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404676B2

Reaction notes

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