Dimethylformamide → HCID 9878166, compound

HRID 431994Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14](I)[CH:13]=2)=[N:10][N:11]=1.[CH3:19][N:20](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:19]#[N:20])[CH:13]=2)=[N:10][N:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Under an argon atmosphere, a mixture of 2-(2-pyridyl)-5-(3-iodophenyl)-1,3,4-oxadiazole (0.03 g, 0.08 mmol), zinc cyanide (0.01 g, 0.12 mmol), and Pd(PPh3)4 (9.1 mg, 0.01 mmol) in N,N-dimethylformamide (2ml) was heated at 80° C. for 2.5 hours. After cooling the reaction mixture was diluted with ethyl acetate and sequentially washed with water (3×50 mL) and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Recrystallization of the crude product from 5% ethyl acetate in hexanes, afforded 5.8 mg (30%) of 2-(2-pyridyl)-5-(3-cyanophenyl)-1,3,4-oxadiazole.

Workup

temperatureAfter cooling the reaction mixture
washsequentially washed with water (3×50 mL) and brine (50 mL)
dry with materialThe organic phase was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customRecrystallization of the crude product from 5% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-20fdf50658a0453ca55d0139b99b71a1
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660753B2

Reaction notes

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