Sodium Carbonate → 2-[1-(4-Nitro-phenyl)-1H-[1,2,3]triazol-4-yl]-pyridine

HRID 1921773Notes

Reaction equation

HRID 1921773 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)#[CH:12].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[Na+].[Na+].[N-:33]=[N+:34]=[N-:35].[Na+].[Na].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].CS(C)=O.O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:33]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[N:35]=[N:34]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

9

Reactant 6

HCID 10340Sodium CarbonateHCID 124951-Iodo-4-nitrobenzeneHCID 33557Sodium AzideHCID 137268EthynylpyridineHCID 145742L-ProlineHCID 178519209sodium (L)-ascorbate

Product 1

HCID 590229972-[1-(4-Nitro-phenyl)-1H-[1,2,3]triazol-4-yl]-pyridineYield 59%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-iodo-4-nitrobenzene (0.513 g, 2.06 mmol), 2-ethynyl pyridine (0.208 mL, 2.06 mmol), L-proline (47.4 mg, 0.412 mmol), Na2CO3 (43.7 mg, 0.412), NaN3 (0.1607 g, 2.47 mmol), (+)-sodium-L-ascorbate (40.8 mg, 0.206 mmol), copper (II) sulphate pentahydrate (16.4 mg, 0.103 mmol) in 9:1 DMSO-water (4 mL) is stirred in a stem-tube at 65° C. for 24 hours. After cooling, the reaction mixture is poured into ice-water (100 mL) and the resulting precipitate is collected by filtration, washed with 7% aq. NH3 and dried in vacuo to give the title compound as a brown solid (0.323 g, 59%). HPLC (254 nm) Rt 2.36 min (89%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate is collected by filtration
  3. washwashed with 7% aq. NH3
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1d2c22447501406fb4237c34ba39d066
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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