5-Azaindole → HCID 66922379, compound

HRID 2039817Notes

Reaction equation

HRID 2039817 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][N:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.N[C@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+].IC1C=CC=CC=1>O1CCOCC1.[Cu]I>[C:11]1([N:1]2[C:9]3[CH:8]=[CH:7][N:6]=[CH:5][C:4]=3[CH:3]=[CH:2]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 92205-AzaindoleHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 4793071,2-Diaminocyclohexane, (+)-

Product 1

HCID 66922379HCID 66922379, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 5-azaindole (780 mg, 6.60 mmol), copper(I) iodide (25.1 mg, 132 μmol), (1S,2S)-(+)-1,2-diaminocyclohexane (162 μl, 1.35 mmol) and potassium phosphate (2.52 g, 11.9 mmol) in dioxane (24 ml) was added iodobenzene (739 μl, 6.60 mmol). The reaction mixture was stirred overnight at 110° C. The mixture was then cooled to room temperature, filtered through silica gel, and the silica gel washed with EA. The combined filtrates was evaporated under reduced pressure, and the resulting solid was purified by preparative HPLC. The fractions containing the title compound were combined and lyophilized overnight. Yield: 1.28 g.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationfiltered through silica gel
  3. washthe silica gel washed with EA
  4. customThe combined filtrates was evaporated under reduced pressure
  5. customthe resulting solid was purified by preparative HPLC
  6. additionThe fractions containing the title compound
  7. waitlyophilized overnight

Sources & evidence

ORD record
ord-38c996eeacc14a7b8ea494a8279a4332
Source dataset
uspto-grants-2013_11
Patent number
US08580813B2

Reaction notes

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