1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 57691340, compound

HRID 1513655Notes

Reaction equation

HRID 1513655 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]3[N:13]=[N:14][C:15]([C:16]([O-:18])=O)=[C:9]3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([CH2:31][C:32]([O:34][CH3:35])=O)[CH:26]=2)C=CC=CC=1.[CH2:36]1CCN2C(=NCCC2)C[CH2:37]1.C(NC1C=CC(S(N=[N+]=[N-])(=O)=O)=CC=1)(=O)C>CC#N>[CH3:35][O:34][C:32]1[CH:31]=[C:27]2[C:26]([C:25]([O:18][CH2:16][C:15]3[N:14]=[N:13][N:10]4[CH:11]=[CH:12][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[CH:8][C:9]=34)=[CH:30][CH:29]=[N:28]2)=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 51291854-Acetamidobenzenesulfonyl azideHCID 67503470Methyl 2-(4-phenylpyridin-2-yl)acetateHCID 86630264HCID 86630264, compound

Product 1

HCID 57691340HCID 57691340, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Phenyl-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylate. To a solution of methyl 2-(4-phenylpyridin-2-yl)acetate (see Lohse, O.; Thevenin, P.; Waldvogel, E. Synlett 1999, 1, 45-48) (0.504 g, 2.22 mmol) in 12 mL CH3CN was added DBU (0.501 ml, 3.33 mmol) and the mixture cooled in an ice bath. To the solution, 4-acetamidobenzenesulfonyl azide (0.533 g, 2.22 mmol) was added and the mixture allowed to warm to rt. The mixture was stirred at rt for 5 h then evaporated. The residue was diluted with CH2Cl2, washed with water, brine, dried over Na2SO4, and filtered. The title compound was obtained after purification via flash chromatography.

Workup

  1. temperaturethe mixture cooled in an ice bath
  2. customthen evaporated
  3. additionThe residue was diluted with CH2Cl2
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-c04133e2a1fb498cbbb157965bd131fe
Source dataset
uspto-grants-2012_07
Patent number
US08217177B2

Reaction notes

Loading…