N-Iodosuccinimide → 5-(4-Iodo-3-(pyridin-2-yl)isoxazol-5-yl)-3-p-tolyl-1,2,4-oxadiazole

HRID 1951931Notes

Reaction equation

HRID 1951931 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:11]=[C:10]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[N:13]=2)[O:9][N:8]=1.[I:24]N1C(=O)CCC1=O>C(#N)C>[I:24][C:11]1[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:8][O:9][C:10]=1[C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:13]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 580628225-(3-(Pyridin-2-yl)isoxazol-5-yl)-3-p-tolyl-1,2,4-oxadiazole

Product 1

HCID 580628235-(4-Iodo-3-(pyridin-2-yl)isoxazol-5-yl)-3-p-tolyl-1,2,4-oxadiazoleYield 378%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-(3-(pyridin-2-yl)isoxazol-5-yl)-3-p-tolyl-1,2,4-oxadiazole (1.0 g, 3.29 mmol), 1-iodopyrrolidine-2,5-dione (1.11 g, 4.76 mmol), and PdOAc2 (0.148 g, 0.657 mmol) in acetonitrile (14 mL) was heated to 120° C. via microwave for 40 minutes. The reaction was repeated 4 additional times on a similar scale, and the contents of each reaction tube were combined, concentrated, and purified by flash silica gel chromatography (eluting with Hexanes/EtOAc—4/1) to yield 5-(4-iodo-3-(pyridin-2-yl)isoxazol-5-yl)-3-p-tolyl-1,2,4-oxadiazole (5.35 g, 76% yield). The compound had an HPLC retention time=3.81 minutes (YMC-Combi 4.6×50 mm S-5 ODS column) eluting with 10-90% aqueous methanol+0.2% phosphoric acid over a 4 minute gradient. MS: (M+H)=431+. 1H NMR (400 MHz, CDCl3) δ ppm 2.46 (s, 3H), 7.36 (d, J=8.03 Hz, 2H), 7.46-7.52 (m, 1H), 7.90 (td, J=7.72, 1.63 Hz, 1H), 8.01 (d, J=7.78 Hz, 1H), 8.12 (d, J=8.28 Hz, 2H), and 8.86 (d, J=4.27 Hz, 1H).

Workup

  1. customthe contents of each reaction tube were combined
  2. concentrationconcentrated
  3. custompurified by flash silica gel chromatography (eluting with Hexanes/EtOAc—4/1)

Sources & evidence

ORD record
ord-9620773fb8bc4397976e313472b67ec2
Source dataset
uspto-grants-2013_03
Patent number
US08404672B2

Reaction notes

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