Benzyl azide → HCID 11165847, compound

HRID 2053436Notes

Reaction equation

HRID 2053436 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH:16][C:17](=[O:21])[CH2:18][C:19]#[CH:20])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([N:29]=[N+:30]=[N-:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>C(O)(C)(C)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:22]([N:29]1[CH:20]=[C:19]([C:18]2[C:17](=[O:21])[NH:16][C:10]3[C:9]([C:1]=2[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][C:13]([Cl:15])=[CH:12][CH:11]=3)[N:31]=[N:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 12152Benzyl azideHCID 23667548Sodium AscorbateHCID 59654916But-3-ynoic acid (2-benzoyl-4-chloro-phenyl)-amide

Product 1

HCID 11165847HCID 11165847, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of but-3-ynoic acid (2-benzoyl-4-chloro-phenyl)-amide (from Example 7) (0.056 g, 0.188 mmol) in 50% aq. tert-butanol (5 mL) was added benzyl azide (0.07 mL, 0.56 mmol), sodium ascorbate (0.012 g, 0.0564 mmol), and copper(II) sulfate pentahydrate (0.002 g, 5.64 μmol). After stirring at 70° C. for 15 hours, the reaction mixture was partitioned between ethyl acetate (15 mL) and water (15 mL). The aqueous layer was further extracted with ethyl acetate (2×15 mL) and the combined organic layers were dried (MgSO4) and concentrated. The residual yellow oil was purified by flash chromatography (silica gel) to afford 3-(1-benzyl-1H-[1,2,3]triazol-4-yl)-6-chloro-4-phenyl-1H-quinolin-2-one (0.064 g, 82% yield) as white solid. 1H NMR (300 MHz, CDCl3): δ 12.42 (s, 1H), 7.51 (s, 1H), 7.39-7.32 (m, 7.5H), 7.29 (s, 0.5H), 7.18-7.15 (m, 3H), 7.09-7.06 (m, 2H), 5.46 (s, 2H). MS: 413 (M+H).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate (15 mL) and water (15 mL)
  2. extractionThe aqueous layer was further extracted with ethyl acetate (2×15 mL)
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residual yellow oil was purified by flash chromatography (silica gel)

Sources & evidence

ORD record
ord-84cc88fac60644868cf493a1c2e055ef
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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