Oxalyl chloride → 5-(2,2'-Dimethylbiphenyl-4-YL)-3-(5-fluoro-2-methoxyphenyl)-1,2,4-oxadiazole

HRID 336272Notes

Reaction equation

HRID 336272 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23].[F:24][C:25]1[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([C:31](=[N:33]O)[NH2:32])[CH:30]=1.CCN(C(C)C)C(C)C>>[CH3:7][C:8]1[CH:13]=[C:12]([C:14]2[O:16][N:32]=[C:31]([C:29]3[CH:30]=[C:25]([F:24])[CH:26]=[CH:27][C:28]=3[O:35][CH3:36])[N:33]=2)[CH:11]=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23]

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 219373032,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acidHCID 723368235-fluoro-N'-hydroxy-2-methoxybenzenecarboximidamide

Product 1

HCID 252563885-(2,2'-Dimethylbiphenyl-4-YL)-3-(5-fluoro-2-methoxyphenyl)-1,2,4-oxadiazole

Procedure

Oxalyl chloride (190 mg; 1.5 mmol; 3 eq.), Intermediate 16 (113 mg; 0.5 mmol; 1 eq.), Intermediate 23 (92 mg; 0.5 mmol, 1 eq.) and DIEA (194 mg; 1.5 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 solid.

Workup

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

Sources & evidence

ORD record
ord-bdd06a22db624850be80f01149604bbb
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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