2-Chlorophenylboronic acid → 3-(2-Chlorophenyl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)furo[3,2-b]pyridine

HRID 452831Notes

Reaction equation

HRID 452831 reaction equation
Br[C:2]1[C:6]2=[N:7][C:8]([C:11]3[O:12][C:13]([CH3:16])=[N:14][N:15]=3)=[CH:9][CH:10]=[C:5]2[O:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O>>[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:2]1[C:6]2=[N:7][C:8]([C:11]3[O:12][C:13]([CH3:16])=[N:14][N:15]=3)=[CH:9][CH:10]=[C:5]2[O:4][CH:3]=1

Participants

3

Reactant 2

HCID 27343222-Chlorophenylboronic acidHCID 686630993-Bromo-5-(5-methyl-1,3,4-oxadiazol-2-yl)furo[3,2-b]pyridine

Product 1

HCID 686636463-(2-Chlorophenyl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)furo[3,2-b]pyridineYield 6%

Procedure

In the same manner as in Example 132 and using 3-bromo-5-(5-methyl-1,3,4-oxadiazol-2-yl)furo[3,2-b]pyridine instead of 2-(3-bromo-1-benzofuran-5-yl)-5-methyl-1,3,4-oxadiazole, using (2-chlorophenyl)boronic acid instead of (4-fluorophenyl)boronic acid, and using [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane complex instead of tetrakis(triphenylphosphine)palladium(0), the title compound (yield 6%) was obtained as colorless crystals.

Sources & evidence

ORD record
ord-ee1fbb1f428e409ebd39ec68a7fefb5e
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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