Triethylamine → HCID 21942432, compound

HRID 2216860Notes

Reaction equation

HRID 2216860 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].C(N(CC)CC)C.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[N:33]=[C:32]([C:34]2[CH:39]=[C:38](O)[CH:37]=[C:36]([C:41]#[N:42])[CH:35]=2)[O:31][N:30]=1>ClCCl>[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[N:33]=[C:32]([C:34]2[CH:39]=[C:38]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:37]=[C:36]([C:41]#[N:42])[CH:35]=2)[O:31][N:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 9878436HCID 9878436, compound

Product 1

HCID 21942432HCID 21942432, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (22.9 μL, 0.14 mmol) and triethylamine (23.7 μL, 0.17) were added under argon to a vial containing 3-(2-pyridyl)-5-(3-cyano-5-hydroxyphenyl)-1,2,4-oxadiazole (30 mg, 0.11 mmol) in dichloromethane (1 mL). The vial was then sealed and the reaction was left stirring overnight at ambient temperature. The reaction mixture was placed directly onto a flash column and purified by eluting with hexanes:ethyl acetate:dichloromethane 3.5:0.5:4 to afford 11 mg (25%) of 3-(2-pyridyl)-5-(3-cyano-5-(trifluoromethylsulfonyloxy)phenyl)-1,2,4-oxadiazole: 1H NMR (CDCl3), δ (ppm): 8.88 (d, 1H), 8.63 (s, 1H), 8.44 (s, 1H), 8.24 (d, 1H), 7.93 (t, 1H), 7.83 (s, 1H), 7.52 (m, 1H).

Workup

  1. customThe vial was then sealed
  2. waitthe reaction was left
  3. custompurified
  4. washby eluting with hexanes:ethyl acetate:dichloromethane 3.5:0.5:4

Sources & evidence

ORD record
ord-7b9c27d9ef94410e821feb15c6606219
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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