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Trifluoroacetic acid → 2-Methyl-3-nitro-6-[1-(phenylmethyl)-3-pyrrolidinyl]pyridine

HRID 594110
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Reaction equation

HRID 594110 reaction equation
[CH:1]([C:3]1[N:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=1)=[CH2:2].FC(F)(F)C(O)=O.CO[CH2:22][N:23]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:24][Si](C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:9][C:7]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=[C:3]([CH:1]2[CH2:2][CH2:24][N:23]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:22]2)[N:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 516892Sodium BicarbonateHCID 684528106-Ethenyl-2-methyl-3-nitropyridine

Product 1

HCID 898759582-Methyl-3-nitro-6-[1-(phenylmethyl)-3-pyrrolidinyl]pyridineYield 25.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of crude 6-ethenyl-2-methyl-3-nitropyridine (440 mg, 2.68 mmol) in dichloromethane (DCM) (5 mL) was added trifluoroacetic acid (0.268 mL, 3.48 mmol). To this stirred solution was added [(methyloxy)methyl](phenylmethyl)[(trimethylsilyl)methyl]amine (2.74 mL, 10.72 mmol) (carefully) and the reaction mixture was stirred under nitrogen for 1.5 hours. The reaction mixture was diluted with DCM and then treated with saturated sodium bicarbonate solution. The organic phase was separated and passed through a hydrophobic frit. The organic solvent was evaporated in vacuo and the residue was dissolved in DCM (5 mL). This was purified by silica (Si) chromatography (0-100% ethyl acetate-cyclohexane with 0-20% methanol gradient). The appropriate fractions were combined and evaporated in vacuo to give the crude product (201 mg) as a brown liquid. Used directly in next step without further purification. LCMS (2 min, formic) Rt 0.71 min, m/z (ES+) 298 (M+H).

Workup

  1. customThe organic phase was separated
  2. customThe organic solvent was evaporated in vacuo
  3. dissolutionthe residue was dissolved in DCM (5 mL)
  4. customThis was purified by silica (Si) chromatography (0-100% ethyl acetate-cyclohexane with 0-20% methanol gradient)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ce0186995fa5451285e11726fe8e67f7
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242972B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes