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

反応式

C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24].O[N:27]=[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][C:37]([F:40])([F:39])[F:38])[NH2:29].CCN(C(C)C)C(C)C>>[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[O:22][N:29]=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][C:37]([F:38])([F:39])[F:40])[N:27]=2)=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24]

参加物

反応物 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

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

HCID 594958102'-Methyl-2-nitro-[1,1'-biphenyl]-4-carboxylic acid

生成物 1

HCID 252563905-(2'-Methyl-2-nitrobiphenyl-4-YL)-3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

実験手順

Oxalyl chloride (118 μL; 1.40 mmol; 3 eq.), Intermediate 22 (120 mg; 0.47 mmol; 1 eq.), Intermediate 2 (103 mg; 0.47 mmol, 1 eq.) and DIEA (103 μL; 1.40 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography c-hexane/ethyl acetate, 90/10) afforded the title compound as a yellow oil.

後処理

customPurification by column chromatography c-hexane/ethyl acetate, 90/10)

出典と根拠

ORDレコード: ord-4d09dd2d0295449896ed5af33b8345ed
出典データセット: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08889668B2

反応ノート

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