HCID 118590347, compound → HCID 118590300, compound

HRID 1054469Notes

Reaction equation

HRID 1054469 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][C@@H:23]2[CH2:27][CH2:26][O:25][CH2:24]2)=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-])=O)=[N:17][CH:18]=2)[CH:7]=1>C(O)C.[Ni]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][C@@H:23]2[CH2:27][CH2:26][O:25][CH2:24]2)=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 118590347HCID 118590347, compound

Product 1

HCID 118590300HCID 118590300, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 5-(2-(5-fluoro-2-(((R)-tetrahydrofuran-3-yl)oxy)phenyl)pyrrolidin-1-yl)-2-nitropyridine (2.8 g, 75.06 mmol) in ethanol (28 ml) was cooled to 10° C. and added Raney Ni (560 mg, 20% w/w) portion wise and stirred for 5 min, then added N2H4.2H2O 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 anhydrous Na2SO4 and concentrated in vacuo to get desired product as brown solid (2.4 g, yield: 93.3%), MS (ESI): 344.2 (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 anhydrous Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-832a4e699b9c4f65aa067e6161e35a0c
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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