Cesium carbonate → HCID 661622, compound

HRID 2177581Notes

Reaction equation

HRID 2177581 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[N:2]1.I[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Cs+].[Cs+].COC1C2C(=C3C(=CC=2)C(OC)=CC=N3)N=CC=1>C(#N)CCC.C(Cl)(Cl)Cl.[Cu-]=O>[C:11]1([N:1]2[C:9]3[CH:8]=[CH:7][N:6]=[CH:5][C:4]=3[N:3]=[N:2]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 104622984,7-Dimethoxy-1,10-phenanthrolineHCID 178419861HCID 178419861, compound

Product 1

HCID 661622HCID 661622, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 6212ChloroformSolventHCID 8008ButyronitrileSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 1H-[1,2,3]-triazolo-[4,5-C]-pyridine (200 mg, 1.7 mmol), iodobenzene (407 mg, 2.0 mmol), Cs2CO3, (1.08 g, 3.3 mmol), copper (I) oxide (17 mg, 0.12 mmol), 4,7-dimethoxy-[1,10]-phenanthroline (84 mg, 0.35 mmol), PEG 400 (0.3 ml) were combined in butyronitrile (3 ml) and heated to 110° C. overnight. The reaction was diluted with CHCl3, filtered through Celite© and then concentrated and purified on 16 g SiO2 with 0-3.5% NH3MeOH in CH2Cl2 to give 52 mg (16%) of 1-phenyl-1H-[1,2,3]triazolo[4,5-c]pyridine. MS (ESI): mass calcd. for C11H8N4, 196.1. m/z found, 197.1 [M+H]+. 1H NMR δ (400 MHz, CDCl3) δ 9.58 (s, 1H), 8.66 (d, J=5.8 Hz, 1H), 7.83-7.75 (m, 2H), 7.72-7.62 (m, 3H), 7.62-7.52 (m, 1H).

Workup

  1. filtrationfiltered through Celite©
  2. concentrationconcentrated
  3. custompurified on 16 g SiO2 with 0-3.5% NH3MeOH in CH2Cl2

Sources & evidence

ORD record
ord-4102b4e1db2f4562a195ca44cc1125c1
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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