Stannous chloride dihydrate → N-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine

HRID 1969800Notes

Reaction equation

HRID 1969800 reaction equation
[CH:1]1([NH:7][C:8]2[C:9]3[CH:19]=[CH:18][NH:17][C:10]=3[N:11]=[CH:12][C:13]=2[N+:14]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl>CCO>[CH:1]1([NH:7][C:8]2[C:13]([NH2:14])=[CH:12][N:11]=[C:10]3[NH:17][CH:18]=[CH:19][C:9]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 58557102N-cyclohexyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-amine

Product 1

HCID 58557425N-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamineYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of N-cyclohexyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-amine (0.15 g, 0.57 mmol) in EtOH (10 mL) was added tin (II) chloride dihydrate (0.65 g, 2.9 mmol). The reaction mixture was heated at about 55° C. for about 1 h. The solvent was removed under reduced pressure and EtOAc (75 mL) and saturated aqueous NaHCO3 (25 mL) were added. The solid that formed was collected by vacuum filtration, washed with EtOAc (25 mL), and discarded. The filtrate was washed with saturated aqueous NaHCO3 (3×20 mL), dried over anhydrous MgSO4, filtered, and concd to give N-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine (0.107 g, 87%) as a brown residue: LC/MS (Table 1, Method c) Rt=1.21 min; MS m/z 231 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure and EtOAc (75 mL) and saturated aqueous NaHCO3 (25 mL)
  2. additionwere added
  3. customThe solid that formed
  4. filtrationwas collected by vacuum filtration
  5. washwashed with EtOAc (25 mL)
  6. washThe filtrate was washed with saturated aqueous NaHCO3 (3×20 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-25a3e11bbedd4cc7ad0f18db647444a1
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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