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

HRID 1696233Notes

Reaction equation

HRID 1696233 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:3]=12.[CH3:14][NH:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)C(C)C)(C)C>CC(O)C>[CH:16]1([N:15]([CH3:14])[C:2]2[C:3]3[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][CH:7]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 7514N-MethylcyclohexylamineHCID 81531DiisopropylethylamineHCID 247295694-Chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 67277161N-cyclohexyl-N-methyl-3-nitro-1H-pyrrolo[2,3-b]pyridin-4-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 4-chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine (57 mg) in 2-propanol (180 μl) were added N-methylcyclohexanamine (154 μl) and N,N-diisopropylethylamine (50 μl), and irradiated microwave at 120° C. for 15 minutes. The reaction mixture was purified by flash column chromatography over silica gel with a EtOAc/methanol (100:0-60:40) as eluant. then by preparative silica gel thin-layer chromatography with EtOAc as eluant to give a solid. The solid was washed with diisopropyl ether to give N-cyclohexyl-N-methyl-3-nitro-1H-pyrrolo[2,3-b]pyridin-4-amine (7.9 mg) as a yellow solid.

Workup

  1. customirradiated microwave at 120° C. for 15 minutes
  2. customThe reaction mixture was purified by flash column chromatography over silica gel with a EtOAc/methanol (100:0-60:40) as eluant
  3. customthen by preparative silica gel thin-layer chromatography with EtOAc as eluant to give a solid
  4. washThe solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-11e8da3d25944bf68af0b609f6cb3f0c
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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