2-Chloro-5-fluorobenzeneboronic acid → (1S)-1-[5-[3-(2-chloro-5-fluorophenyl)-1-benzofuran-5-yl]-1,3,4-oxadiazol-2-yl]ethyl acetate

HRID 452659Notes

Reaction equation

HRID 452659 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].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1B(O)O>>[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:28]4[CH:27]=[C:26]([F:29])[CH:25]=[CH:24][C:23]=4[Cl:22])[C:16]=3[CH:21]=2)=[N:10][N:11]=1)[CH3:6])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 226481162-Chloro-5-fluorobenzeneboronic acidHCID 68663008(1S)-1-[5-(3-bromo-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]ethyl acetate

Product 1

HCID 68663011(1S)-1-[5-[3-(2-chloro-5-fluorophenyl)-1-benzofuran-5-yl]-1,3,4-oxadiazol-2-yl]ethyl acetateYield 66%

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 (2-chloro-5-fluorophenyl)boronic acid instead of (4-methoxyphenyl)boronic acid, the title compound (yield 66%) was obtained as colorless crystals.

Sources & evidence

ORD record
ord-407825aeea0443f992b67c6b59b790a5
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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