4-(Methylthio)phenylboronic acid → (1S)-1-[5-[3-[4-(methylthio)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazol-2-yl]ethyl acetate

HRID 452657Notes

Reaction equation

HRID 452657 reaction equation
[C:1]([O:4][C@H:5]([C:7]1[O:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:19][CH:18]=[C:17](Br)[C:16]=3[CH:21]=2)=[N:10][N:11]=1)[CH3:6])(=[O:3])[CH3:2].[CH3:22][S:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>>[C:1]([O:4][C@H:5]([C:7]1[O:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:19][CH:18]=[C:17]([C:27]4[CH:28]=[CH:29][C:24]([S:23][CH3:22])=[CH:25][CH:26]=4)[C:16]=3[CH:21]=2)=[N:10][N:11]=1)[CH3:6])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 27339594-(Methylthio)phenylboronic acidHCID 68663008(1S)-1-[5-(3-bromo-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]ethyl acetate

Product 1

HCID 68664217(1S)-1-[5-[3-[4-(methylthio)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazol-2-yl]ethyl acetateYield 64%

Procedure

In the same manner as in Reference Example 19 and using (1S)-1-[5-(3-bromo-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]ethyl acetate instead of methyl 3-iodoimidazo[1,2-a]pyridine-6-carboxylate and [4-(methylthio)phenyl]boronic acid instead of (4-methoxyphenyl)boronic acid, the title compound (yield 64%) was obtained as colorless crystals.

Sources & evidence

ORD record
ord-aea6619d4b4046d480f49b6c5712fc70
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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