HCID 118590318, compound → HCID 118590405, compound

HRID 1054436Notes

Reaction equation

HRID 1054436 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:15]=[CH:16][C:17]([N+:20]([O-])=O)=[N:18][CH:19]=1>C(O)C.[Ni]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=1

Participants

4

Reactant 1

HCID 118590318HCID 118590318, compound

Product 1

HCID 118590405HCID 118590405, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-2-nitropyridine (3.2 g, 10.46 mmol) in Ethanol (32 ml) was cooled to 10° C. and added Raney Ni (640 mg, 20% w/w) portion wise and stirred for 5 min, then added N2H4.2H2O (1.05 g, 20.98 mmol) drop wise for the period of 5 min, then stirred for 20 min at room temperature. After completion of reaction, reaction mixture was filter through celite bed under N2 atmosphere and filtrate was concentration under reduced pressure, the residue was re-dissolved in DCM and washed with water, brine and dried over Na2SO4 and concentration to get desired product as brown solid (2.7 g, 93% yield), MS (ESI): m/z 276.1 (M+H).

Workup

  1. customAfter completion of reaction, reaction mixture
  2. filtrationwas filter through celite bed under N2 atmosphere
  3. concentrationconcentration under reduced pressure
  4. dissolutionthe residue was re-dissolved in DCM
  5. washwashed with water, brine
  6. dry with materialdried over Na2SO4 and concentration

Sources & evidence

ORD record
ord-7f4fa33c20ca4665a62e4ae630906ea5
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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