Tetrahydrofuran → {5-[5-(3-Fluoro-4-phenoxyphenyl]-1,2,4-oxadiazol-3-yl)-4-methyl-2-thienyl}methanol

HRID 2247696Notes

Reaction equation

HRID 2247696 reaction equation
[Si]([O:8][CH2:9][C:10]1[S:14][C:13]([C:15](=[N:17][OH:18])[NH2:16])=[C:12]([CH3:19])[CH:11]=1)(C(C)(C)C)(C)C.[F:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:24](O)=O.C1(N=C=NC2CCCCC2)CCCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[F:20][C:21]1[CH:22]=[C:23]([C:24]2[O:18][N:17]=[C:15]([C:13]3[S:14][C:10]([CH2:9][OH:8])=[CH:11][C:12]=3[CH3:19])[N:16]=2)[CH:27]=[CH:28][C:29]=1[O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 2724141Tetrabutylammonium FluorideHCID 286051153-Fluoro-4-phenoxybenzoic acidHCID 86620222HCID 86620222, compound

Product 1

HCID 68525640{5-[5-(3-Fluoro-4-phenoxyphenyl]-1,2,4-oxadiazol-3-yl)-4-methyl-2-thienyl}methanol

Procedure

The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 10 (10f) using 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-N′-hydroxy-3-methylthiophene-2-carboximidamide (0.18 g, 0.60 mmol) that was obtained in Example 11 (11d), 3-fluoro-4-phenoxybenzoic acid (0.15 g, 0.66 mmol) that was obtained in Example 11 (11e), N,N′-dicyclohexylcarbodiimide (0.14 g, 0.66 mmol), and 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.90 mL, 0.90 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:1) as the eluent to afford the title compound (0.21 g) in a yield of 93% as a white crystalline solid.

Workup

  1. customthe reaction similar to

Sources & evidence

ORD record
ord-623c14aebd9b4525beb117deca00a5aa
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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