2-Chloro-5-nitropyridine → HCID 67237449, compound

HRID 1471008Notes

Reaction equation

HRID 1471008 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.Cl.[F:12][C:13]1([F:19])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(CC)C(C)C)(C)C>C(O)C>[F:12][C:13]1([F:19])[CH2:18][CH2:17][N:16]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 783082-Chloro-5-nitropyridineHCID 81531DiisopropylethylamineHCID 27583514,4-Difluoropiperidine hydrochloride

Product 1

HCID 67237449HCID 67237449, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a slurry of 2-chloro-5-nitropyridine (5 g, 31.5 mmol) and 4,4-difluoropiperidine hydrochloride (4.97 g) in ethanol (40 mL) at ambient temperature was added N,N-diisopropylethylamine (12.00 mL, 69.4 mmol) and the mixture heated to 70° C. for 18 hours. The reaction was concentrated, partitioned between CH2Cl2 and 1M NaOH. The organic phase concentrated and purified by chromatography (elution with 2% MeOH—CH2Cl2 then 3% MeOH—CH2Cl2) to provide the title compound as a yellow oil. MS (DCI) m/z 261 (M+NH4)+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompartitioned between CH2Cl2 and 1M NaOH
  3. concentrationThe organic phase concentrated
  4. custompurified by chromatography (
  5. washelution with 2% MeOH—CH2Cl2

Sources & evidence

ORD record
ord-b2bb9456c7184df290dd2f6a475cf0a3
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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