2-Fluoropyridine-5-carbonyl chloride → 3-(5-(6-Fluoropyridin-3-yl)-1,2,4-oxadiazol-3-yl)benzonitrile

HRID 450593Notes

Reaction equation

HRID 450593 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6](=[N:8][OH:9])[NH2:7])#[N:2].[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=O)=[CH:16][N:15]=1>N1C=CC=CC=1>[F:13][C:14]1[N:15]=[CH:16][C:17]([C:18]2[O:9][N:8]=[C:6]([C:5]3[CH:4]=[C:3]([CH:12]=[CH:11][CH:10]=3)[C:1]#[N:2])[N:7]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 146236022-Fluoropyridine-5-carbonyl chlorideHCID 573689333-Cyano-N-hydroxy-benzamidine

Product 1

HCID 670259663-(5-(6-Fluoropyridin-3-yl)-1,2,4-oxadiazol-3-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Cyano-N′-hydroxybenzimidamide (0.322 g, 1 mmol) was dissolved in pyridine 10 mL and 6-fluoronicotinoyl chloride (Frontier Scientific, 0.160 g, 1 mmol) was added. The reaction mixture was heated to reflux for 3 hours and then cooled to room temperature. The cooled reaction mixture was quenched with water (25 mL) and filtered. The solid was further purified with flash column chromatography (5% methanol/dichloromethane) to give the titled product. 1H NMR (300 MHz, DMSO-d6) δ 7.56-7.52 (m, 1 H), 7.85 (t, J=7.9 Hz, 1 H), 8.15-8.12 (m, 1 H), 8.43-8.41 (m, 1 H), 8.49 (m, 1 H), 8.8-8.74 (m, 1 H), 9.11-9.0 (m, 1 H) ppm; MS (DCI/NH3) m/z 267 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe cooled reaction mixture
  4. customwas quenched with water (25 mL)
  5. filtrationfiltered
  6. customThe solid was further purified with flash column chromatography (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-543e11d18deb4aa1a479123e021b1a73
Source dataset
uspto-grants-2013_07
Patent number
US08486979B2

Reaction notes

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