Diazomethane → HCID 21942480, compound

HRID 431979Notes

Reaction equation

HRID 431979 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]([C:19]4[NH:23][N:22]=[N:21][N:20]=4)[CH:16]=[C:15]([F:24])[CH:14]=3)[O:10][N:9]=2)=[N:6][CH:7]=1.[N+](=[CH2:27])=[N-]>O1CCCC1>[F:24][C:15]1[CH:14]=[C:13]([C:11]2[O:10][N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=3)[N:12]=2)[CH:18]=[C:17]([C:19]2[N:23]([CH3:27])[N:22]=[N:21][N:20]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 178505599HCID 178505599, compound

Product 1

HCID 21942480HCID 21942480, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-fluoro-pyrid-2-yl)-5-[3-fluoro-5-(1H-tetraazol -5-yl)-phenyl]-1,2,4-oxadiazole (30mg, 0.092 mmol) in tetrahydrofuran (1 mL), 0.5 M diazomethane (1 mL, 0.5 mmol, ether) was added. The reaction was quenched with water and extracted with dichloromethane. The product was purified by column chromatography with 20% ethyl acetate in hexanes to give 6.7 mg (21.4%) of 5-[3-fluoro -5-(1-methyl-1H-tetraazol-5-yl)-phenyl]-3-(5-fluoro-pyrid-2-yl)-1,2,4-oxadiazole. 1H-NMR (CDCl3), δ (ppm): 8.87 (s, 1H), 8.70 (d, 1H), 8.29 (dd, 1H), 8.10 (m, 2H), 7.62 (dt, 1H), 4.46 (s, 3H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. customThe product was purified by column chromatography with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7f2817244a784030983db825966b2d61
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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