Cesium carbonate → HCID 66704216, compound

HRID 424838Notes

Reaction equation

HRID 424838 reaction equation
[CH:1]([C:4]1[N:8]=[N:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:16]([F:19])([F:18])[F:17])[C:5]=1[CH2:20][OH:21])([CH3:3])[CH3:2].Cl[C:23]1[N:28]=[C:27]([CH3:29])[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:1]([C:4]1[N:8]=[N:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:16]([F:17])([F:19])[F:18])[C:5]=1[CH2:20][O:21][C:23]1[N:28]=[C:27]([CH3:29])[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][CH:24]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2531236-Chloro-2-methyl-3-nitropyridineHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 66704061HCID 66704061, compound

Product 1

HCID 66704216HCID 66704216, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To an ambient temperature solution of [5-isopropyl-3-(2-trifluoromethoxy-phenyl)-3H-[1,2,3]triazol-4-yl]-methanol (2.0 g, 6.64 mmol) in degassed toluene (22 mL) are added 6-chloro-2-methyl-3-nitro-pyridine (1.15 g, 6.64 mmol), cesium carbonate (3.25 g, 9.96 mmol), 2-(di-t-butylphosphino)-1,1′-binapthyl (332 mg, 0.833 mmol, 12.5 mol %), and palladium (II) acetate (150 mg, 0.666 mmol, 10 mol %). The reaction mixture is heated to 70° C. overnight. The reaction is filtered through a pad of diatomaceous earth. The filtrate is concentrated and the residue is chromatographed (SiO2 120 g, 0% to 20% EtOAc/Hexane to yield 6-[5-Isopropyl-3-(2-trifluoromethoxy-phenyl)-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-3-nitro-pyridine (2.78 g, 96%). 1H NMR (400 MHz, CDCl3) δ 8.23 (d, 1H, J=8.8 Hz), 7.61-7.53 (m, 2H), 7.48-7.42 (m, 2H), 6.51 (d, 1H, J=8.8 Hz), 5.42 (s, 2H), 3.26 (sept, 1H, J=7.0 Hz), 2.71 (s, 3H), 1.43 (d, 6H, J=7.0 Hz).

Workup

  1. filtrationThe reaction is filtered through a pad of diatomaceous earth
  2. concentrationThe filtrate is concentrated
  3. customthe residue is chromatographed (SiO2 120 g, 0% to 20% EtOAc/Hexane

Sources & evidence

ORD record
ord-10bd56913f6b467b9c9e1c5ceb8acdf8
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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