1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(4-(Azidomethyl)phenyl)-3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazole

HRID 1172935Notes

Reaction equation

HRID 1172935 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C1CCN2C(=NCCC2)CC1.P([N:52]=[N+:53]=[N-:54])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.C([O-])(O)=O.[Na+]>C1COCC1.CCOCC>[N:52]([CH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[O:14][N:13]=[C:12]([C:4]3[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[C:2]([Cl:1])[CH:3]=3)[N:16]=2)=[CH:18][CH:19]=1)=[N+:53]=[N-:54]

Participants

7

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 516892Sodium BicarbonateHCID 59556551(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)methanol

Product 1

HCID 595565965-(4-(Azidomethyl)phenyl)-3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazoleYield 61.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)methanol (0.100 g, 0.290 mmol) in THF (1.5 ml) was added DBU (0.048 ml, 0.319 mmol) followed by diphenyl phosphorazidate (0.069 ml, 0.319 mmol). After about 15 h the reaction mixture was poured into ether and saturated NaHCO3. The organic layer was separated, washed with brine, dried (MgSO4), concentrated in vacuo and purified by chromatography on silica gel (eluting with EtOAc/Hep) to provide 5-(4-(azidomethyl)phenyl)-3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazole (0.066 g, 60%) as a colorless solid. LCMS (Table 1, Method c) Rt=3.22 min, m/z 370 (M+H)+

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography on silica gel (eluting with EtOAc/Hep)

Sources & evidence

ORD record
ord-7360712153c949788c4f2a31abf877b8
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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