Water → HCID 90046196, compound

HRID 1482909Notes

Reaction equation

HRID 1482909 reaction equation
[N:1]1[NH:2][N:3]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:5]=1.[F:11][C:12]([F:24])([F:23])[O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.N1C=CC=CC=1.O>CC(N(C)C)=O.C(O[Cu]OC(=O)C)(=O)C.C(OCC)(=O)C>[F:11][C:12]([F:23])([F:24])[O:13][C:14]1[CH:19]=[CH:18][C:17]([N:2]2[N:3]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:5]=[N:1]2)=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 6419107ethyl 1H-1,2,3-triazole-4-carboxylate

Product 1

HCID 90046196HCID 90046196, compoundYield 24.2%

Reagents, catalysts & solvents 3

HCID 178476681HCID 178476681, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

Ethyl 2H-1,2,3-triazole-4-carboxylate (CAS 1084802-21-0) (250 mg, 1.77 mmol, Eq: 1.00), 4-(trifluoromethoxy)phenylboronic acid (730 mg, 3.54 mmol, Eq: 2) and diacetoxy copper (644 mg, 3.54 mmol, Eq: 2) were dissolved in DMA (8.86 ml). Then pyridine (560 mg, 572 μl, 7.09 mmol, Eq: 4) was added and the reaction mixture was stirred at rt for 48 hours. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with brine, dried over MgSO4 and evaporated. The crude material was purified by silica gel flash chromatography to yield a white solid (129 mg, 24%). MS (ISP): 302.1 ([M+H]+).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe crude material was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-716f33f285544994ae3756aa911c88da
Source dataset
uspto-grants-2016_08
Patent number
US09416127B2

Reaction notes

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