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

HRID 2216859Notes

Reaction equation

HRID 2216859 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

Conditions

Temperature
78 °C

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° C. 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. temperatureThe reaction was cooled
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customfollowed by recrystallization

Sources & evidence

ORD record
ord-aa15ea65a3394ab78dff096b1a44e2a9
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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