1,2-Diaminocyclohexane, trans- → HCID 21110082, compound

HRID 1766161Notes

Reaction equation

HRID 1766161 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:9][S:10]([C:13]1[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=1)(=[O:12])=[O:11].[C@@H]1(N)CCCC[C@H]1N.[NH:28]1[C:32]2=[N:33][CH:34]=[CH:35][CH:36]=[C:31]2[C:30]([C:37]([O:39][CH3:40])=[O:38])=[CH:29]1>CCCCCCCCCCCC.O1CCOCC1.ClCCl>[CH3:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([N:28]2[C:32]3=[N:33][CH:34]=[CH:35][CH:36]=[C:31]3[C:30]([C:37]([O:39][CH3:40])=[O:38])=[CH:29]2)=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

8

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 770141-Bromo-4-(methylsulphonyl)benzeneHCID 21110084methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate

Product 1

HCID 21110082HCID 21110082, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8182DodecaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

0.038 g (0.2 mmol) of cuprous iodide, 0.891 g (4.2 mmol) of potassium phosphate, 0.47 g (2 mmol) of 4-bromophenyl methyl sulfone and 0.24 cm3 (2 mmol) of trans-1,2-cyclohexanediamine were added, under an argon atmosphere, to 0.405 g (2.3 mmol) of methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate in solution in 0.3 cm3 of dodecane and 6 cm3 of dioxane. After stirring at a temperature in the region of 110° C. for 48 h, the reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which was taken up in 20 cm3 of dichloromethane. The resulting organic solution was washed with 20 cm3 of 0.1N hydrochloric acid and filtered, then dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). Methyl 1-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate, characterized by LC/MS (m/z 331 [MH]+), was thus obtained, which was used directly in the following stage.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa)
  2. customto give a residue which
  3. washThe resulting organic solution was washed with 20 cm3 of 0.1N hydrochloric acid
  4. filtrationfiltered
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customwas thus obtained

Sources & evidence

ORD record
ord-98638b34f0214989bc32980c74fc65a1
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

Loading…