3-(2-Pyridyl)-5-(3-cyano-5-vinylphenyl)-1,2,4-oxadiazole → 3-(2-Pyridyl)-5-(3-cyano-5-(2-hydroxyethyl)phenyl)-1,2,4-oxadiazole

HRID 431952Notes

Reaction equation

HRID 431952 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([CH:18]=[CH2:19])[CH:15]=[C:14]([C:20]#[N:21])[CH:13]=2)[O:9][N:8]=1.C12CCCC(CCC1)B12[H]B2(C3CCCC2CCC3)[H]1.B1([O-])O[O:43]1.O.O.O.O.[Na+]>ClCCl.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([CH2:18][CH2:19][OH:43])[CH:15]=[C:14]([C:20]#[N:21])[CH:13]=2)[O:9][N:8]=1

Participants

5

Reactant 2

HCID 99216423-(2-Pyridyl)-5-(3-cyano-5-vinylphenyl)-1,2,4-oxadiazoleHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 99006703-(2-Pyridyl)-5-(3-cyano-5-(2-hydroxyethyl)phenyl)-1,2,4-oxadiazoleYield 3.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-(2-pyridyl)-5-(3-cyano-5-vinylphenyl)-1,2,4-oxadiazole (83 mg, 0.30 mmol) in dichloromethane (2 mL) was treated with 9-BBN dimer (40 mg, 0.16 mmol) and the reaction mixture stirred at room temperature for 4 hours. Sodium perborate tetrahydrate (157 mg, 1.02 mmol) and water (1 mL) were added and the resulting biphasic mixture was stirred vigorously for 18 hours. The mixture was diluted with dichloromethane and water and the organic layer dried by filtration through an EX-TUBE. Silica gel chromatography using a gradient of 20% to 75% ethyl acetate in hexane, followed by trituration in 10% ethyl acetate in hexane afforded 3.4 mg (3.7%) of 3-(2-pyridyl)-5-(3-cyano-5-(2-hydroxyethyl)phenyl)-1,2,4-oxadiazole: 1H-NMR (CDCl3), δ (ppm):08.85 (d, 1H), 8.43 (s, 2H), 8.22 (d, 1H), 7.90 (t, 1H), 7.80 (s, 1H), 7.48 (m, 1H), 3.99 (m, 2H), 3.02 (t, 2H).

Workup

  1. stirringthe resulting biphasic mixture was stirred vigorously for 18 hours
  2. customthe organic layer dried by filtration through an EX-TUBE

Sources & evidence

ORD record
ord-8cc89a9818f54fe188c73a4ef7a76dd0
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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