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

HRID 1951930Notes

Reaction equation

HRID 1951930 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.[Br:24]N1C(=O)CCC1=O>C(#N)C>[Br: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 67184N-bromobutanimideHCID 580628225-(3-(Pyridin-2-yl)isoxazol-5-yl)-3-p-tolyl-1,2,4-oxadiazole

Product 1

HCID 580628455-(4-Bromo-3-(pyridin-2-yl)isoxazol-5-yl)-3-p-tolyl-1,2,4-oxadiazoleYield 393.3%

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 (655 mg, 2.15 mmol), N-bromosuccinimide (536 mg, 3.01 mmol), and PdOAc2 (97 mg, 0.430 mmol) in acetonitrile (12 mL) was heated to 120° C. via microwave for 30 minutes. The reaction was repeated three additional times on a similar scale, and the contents of each reaction tube were combined and filtered. The solid was collected, triturated with methanol (10 mL), and collected by vacuum filtration to give 5-(4-bromo-3-(pyridin-2-yl)isoxazol-5-yl)-3-p-tolyl-1,2,4-oxadiazole (3.24 g, 87% yield). The compound had an HPLC retention time=3.96 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)=385+. 1H NMR (400 MHz, CDCl3) δ ppm 2.46 (s, 3H), 7.35 (d, J=8.03 Hz, 2H), 7.49 (ddd, J=7.65, 4.89, 1.00 Hz, 1H), 7.91 (td, J=7.78, 1.76 Hz, 1H), 8.03 (d, J=7.78 Hz, 1H), 8.12 (d, J=8.28 Hz, 2H), and 8.86 (d, J=4.77 Hz, 1H).

Workup

  1. customthe contents of each reaction tube were combined
  2. filtrationfiltered
  3. customThe solid was collected
  4. customtriturated with methanol (10 mL)
  5. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-51d07ee4627c454c97b00a485ea51742
Source dataset
uspto-grants-2013_03
Patent number
US08404672B2

Reaction notes

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