Water → 5-((2R,4S)-4-fluoro-2-(5-fluoro-2-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)pyrrolidin-1-yl)-2-nitropyridine

HRID 1054461Notes

Reaction equation

HRID 1054461 reaction equation
Cl.[F:2][C@@H:3]1[CH2:7][NH:6][C@@H:5]([C:8]2[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=2[O:15][CH:16]2[CH2:20][CH2:19][O:18][CH2:17]2)[CH2:4]1.C([O-])([O-])=O.[K+].[K+].F[C:28]1[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[N:32][CH:33]=1.O>CN(C=O)C>[F:2][C@@H:3]1[CH2:7][N:6]([C:28]2[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[N:32][CH:33]=2)[C@@H:5]([C:8]2[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=2[O:15][C@H:16]2[CH2:20][CH2:19][O:18][CH2:17]2)[CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 167481095-Fluoro-2-nitropyridineHCID 118590490(2R,4S)-4-fluoro-2-(5-fluoro-2-((tetrahydrofuran-3-yl)oxy)phenyl)pyrrolidine hydrochloride

Product 1

HCID 1185905835-((2R,4S)-4-fluoro-2-(5-fluoro-2-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)pyrrolidin-1-yl)-2-nitropyridineYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2R,4S)-4-fluoro-2-(5-fluoro-2-((tetrahydrofuran-3-yl)oxy)phenyl)pyrrolidine hydrochloride (4.74 g, 15.49 mmol) in dry DMF (20 ml), was added K2CO3 (4.85 g, 35.2 mmol) and stirred for 5 min at room temperature, then added 5-fluoro-2-nitropyridine (2.0 g, 14.08 mmol) under N2 atmosphere and stirred for 16 h at 80° C. After completion of reaction, poured the reaction mixture in ice cooled water and stirred for 10 min, solid precipitated was collected by filtration. Solid was dried under high vacuum to afford 5-((2R,4S)-4-fluoro-2-(5-fluoro-2-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)pyrrolidin-1-yl)-2-nitropyridine as yellow solid (5.1 g, yield: 93%) MS (ESI): 392.1 (M+H).

Workup

  1. customAfter completion of reaction
  2. additionpoured the reaction mixture in ice
  3. stirringstirred for 10 min
  4. customsolid precipitated
  5. filtrationwas collected by filtration
  6. customSolid was dried under high vacuum

Sources & evidence

ORD record
ord-da8e32e0b2cf454485a4634b9373e545
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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