2-Chloro-5-nitropyridine → HCID 57647141, compound

HRID 1714884Notes

Reaction equation

HRID 1714884 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[F:11][C:12]([F:27])([F:26])[C:13]1[CH:25]=[CH:24][CH:23]=[CH:22][C:14]=1[O:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:19]2[CH2:18][CH2:17][CH:16]([O:15][C:14]3[CH:22]=[CH:23][CH:24]=[CH:25][C:13]=3[C:12]([F:11])([F:26])[F:27])[CH2:21][CH2:20]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 783082-Chloro-5-nitropyridineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 50187904-[2-(Trifluoromethyl)phenoxy]piperidine

Product 1

HCID 57647141HCID 57647141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
82.5 °C

Procedure

A mixture of 2-chloro-5-nitropyridine (1.6 g, 6.5 mmol), 4-[2-(trifluoromethyl)phenoxy]piperidine (1.2 g, 7.6 mmol), and DBU (2 mL, 13 mmol) in DMF (25 mL) was heated at 80-85° C. for 2 h. The EtOAc extract was washed three times with water, dried (MgSO4) and concentrated. CombiFlash chromatography (120 g, 20-40% EtOAc in hexanes in 20 min, 70 mL/min, 18 mL/fraction) gave the desired product as a yellow powder.

Workup

  1. extractionThe EtOAc extract
  2. washwas washed three times with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d0f67c795a44447c8ed6e9447764c988
Source dataset
uspto-grants-2010_09
Patent number
US07799787B2

Reaction notes

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