1H-Pyrrolo(2,3-b)pyridine → HCID 18372148, compound

HRID 1678110Notes

Reaction equation

HRID 1678110 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[Cu](I)I.N[C@@H]1CCCC[C@H]1N.O1CCOCC1>[C:19]1([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][N:8]=3)[CH:3]=[CH:2]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 11575IodobenzeneHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 18372148HCID 18372148, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 438061,2-Diaminocyclohexane, trans-CatalystHCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 7-azaindole (550 mg, 4.66 mmol), copper iodide (7.4 mg, 0.038 mmol) and potassium phosphate (1.74 g, 8.18 mmol) under a N2 atmosphere is added racemic trans-1,2-diaminocyclohexane (0.046 mL, 0.38 mmol), iodobenzene (0.436 mL, 3.9 mmol) followed by anhydrous dioxane (5 mL). The resulting suspension is heated in an oil bath at 110° C. with magnetic stirring for 24 hours. The resulting mixture is filtered through a short pad of silica gel, washing the cake well with ethyl acetate. The filtrate is evaporated to leave a brown oil. The residue is purified by flash chromatography on a 10-gram silica gel cartridge by elution with heptane:ethyl acetate (4:1). Fractions containing the product are combined and the solvent evaporated, and further purified by flash chromatography on a 10-gram silica gel cartridge by elution with heptane:ethyl acetate (19:1). Clean fractions containing the product are combined and evaporated to give 758 mg of 1-phenyl-7-azaindole as a light brown oil (100% yield). 1H NMR (300 MHz, CDCl3): 8.37 (1H, dd), 7.97 (1H, dd), 7.76 (2H, d), 7.56-7.49 3H m), 7.35 (1H, t), 7.13 (1H, dd), 6.63 (1H, d).

Workup

  1. filtrationThe resulting mixture is filtered through a short pad of silica gel
  2. washwashing the cake well with ethyl acetate
  3. customThe filtrate is evaporated
  4. customto leave a brown oil
  5. customThe residue is purified by flash chromatography on a 10-gram silica gel cartridge by elution with heptane:ethyl acetate (4:1)
  6. additionFractions containing the product
  7. customthe solvent evaporated
  8. customfurther purified by flash chromatography on a 10-gram silica gel cartridge by elution with heptane:ethyl acetate (19:1)
  9. additionClean fractions containing the product
  10. customevaporated

Sources & evidence

ORD record
ord-9e589445d73e4bba9cffa0d4c35c59e9
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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