Dichloromethane → 3-(5-Fluoropyrid-2-yl)-5-(3-amino-5-cyanophenyl)-1,2,4-oxadiazole

HRID 431967Notes

Reaction equation

HRID 431967 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[C:15]([C:22]#[N:23])[CH:14]=3)[O:10][N:9]=2)=[N:6][CH:7]=1.O.O.[Sn](Cl)Cl.ClCCl>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:14]=[C:15]([C:22]#[N:23])[CH:16]=[C:17]([NH2:19])[CH:18]=3)[O:10][N:9]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 61436Stannous chloride dihydrateHCID 21942561HCID 21942561, compound

Product 1

HCID 219426623-(5-Fluoropyrid-2-yl)-5-(3-amino-5-cyanophenyl)-1,2,4-oxadiazoleYield 23.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(5-fluoropyrid-2-yl)-5-(3-cyano-5-nitrophenyl)-1,2,4-oxadiazole (30 mg, 0.096 mmol) and tin(II) chloride dihydrate (109 mg, 0.48 mmol) in ethanol (1 mL) were sealed in a glass vial and then heated at 78 oC for 2 hours. The reaction was cooled and dichloromethane was added to the reaction mixture. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Silica gel chromatography of the residue using hexanes:ethyl acetate:dichloromethane 1:3:4 followed by recrystallization using methanol afforded 6.3 mg (23%) of 3-(5-fluoropyrid-2-yl)-5-(3-amino-5-cyanophenyl)-1,2,4-oxadiazole: 1H NMR (CDCl3), δ (ppm): 8.69 (d, 1H), 8.25 (m, 1H), 7.89 (s, 1H), 7.76 (s, 1H), 7.61 (m, 1H), 7.11 (s, 1H), 4.17 (bs, 2H).

Workup

  1. temperatureheated at 78 oC for 2 hours
  2. temperatureThe reaction was cooled
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customfollowed by recrystallization

Sources & evidence

ORD record
ord-38bcaeabef674b87a78d2a7b91a2e517
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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