Cyclohexylamine → N-cyclohexyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-amine

HRID 1969799Notes

Reaction equation

HRID 1969799 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]2[NH:11][CH:12]=[CH:13][C:3]=12.[CH:14]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>CN(C=O)C>[CH:14]1([NH:20][C:2]2[C:3]3[CH:13]=[CH:12][NH:11][C:4]=3[N:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 585572594-Chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 58557102N-cyclohexyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-amineYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (0.182 g, 0.921 mmol) in DMF (5 mL) was added cyclohexylamine (0.55 g, 5.5 mmol). The reaction mixture was stirred at ambient temperature for about 2 h. The solvent was removed under reduced pressure and EtOAc (100 mL) and water (20 mL) were added. The layers were separated and the organic layer was washed with water (3×25 mL) and brine (20 mL), dried over anhydrous MgSO4, filtered, and concd to give N-cyclohexyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-amine (0.20, 57%) as a brown residue: LC/MS (Table 1, Method c) Rt=1.53 min; MS m/z 261 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure and EtOAc (100 mL) and water (20 mL)
  2. additionwere added
  3. customThe layers were separated
  4. washthe organic layer was washed with water (3×25 mL) and brine (20 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b00c53c84115435bac3b67aff09387c0
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

Loading…