1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 3-(1-benzyl-1H-pyrazol-4-yl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)furo[3,2-b]pyridine

HRID 452835Notes

Reaction equation

HRID 452835 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.[CH2:17]([N:24]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[N:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([N:24]1[CH:28]=[C:27]([C:2]2[C:6]3=[N:7][C:8]([C:11]4[O:12][C:13]([CH3:16])=[N:14][N:15]=4)=[CH:9][CH:10]=[C:5]3[O:4][CH:3]=2)[CH:26]=[N:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 27347711-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 686630993-Bromo-5-(5-methyl-1,3,4-oxadiazol-2-yl)furo[3,2-b]pyridine

Product 1

HCID 686637963-(1-benzyl-1H-pyrazol-4-yl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)furo[3,2-b]pyridineYield 68%

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 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 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 68%) was obtained as colorless crystals.

Sources & evidence

ORD record
ord-099c9730de404dbf9a8b878d0331b1cf
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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