Potassium Hydroxide → HCID 89807054, compound

HRID 1399979Notes

Reaction equation

HRID 1399979 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]Br)[CH:5]=[CH:4][N:3]=1.[OH-].[K+].Cl.[F:13][C@H:14]1[CH2:18][CH2:17][NH:16][CH2:15]1>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][N:16]2[CH2:17][CH2:18][CH:14]([F:13])[CH2:15]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 129548062-Bromo-4-(bromomethyl)pyridineHCID 16217739(s)-3-Fluoropyrrolidine hydrochloride

Product 1

HCID 89807054HCID 89807054, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To an ice-cold solution of ii (3.0 g, 11.95 mmol) in DMSO (10 mL) was added KOH (1.0 g, 17.92 mmol) followed by the addition of (S)-3-fluoropyrrolidine hydrochloride (2.2 g, 17.92 mmol) under inert atmosphere. The mixture was stirred at 0° C. to RT for 20 min. The mixture was diluted with ice cold H2O followed by extraction with EtOAc (3×150 mL). The combined organic layers were washed with brine, dried (Na2SO4) and evaporated in vacuo to give Precursor 44 (3.0 g, 96%).

Workup

  1. additionThe mixture was diluted with ice cold H2O
  2. extractionfollowed by extraction with EtOAc (3×150 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-24ef08f52a104b1cb9ac949683b10c07
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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