Water → HCID 86689572, compound

HRID 1853930Notes

Reaction equation

HRID 1853930 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH:12]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13]1.C(=O)(O)[O-].[Na+].O>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([N:12]2[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:13]2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 27569932-Bromo-4-fluoro-1-nitrobenzene

Product 1

HCID 86689572HCID 86689572, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-bromo-4-fluoro-1-nitrobenzene (1.5 g, 6.8 mmol), (S)-tert-butyl pyrrolidin-3-ylcarbamate (1.9 g, 10 mmol), and sodium bicarbonate (1.7 g, 20 mmol) in DMSO (40 mL) was heated at 80° C. for 1 h. The reaction mixture was cooled to room temperature, poured into excess water and the resulting precipitate was filtered. The solids were washed with aqueous ammonium chloride, brine and water to afford the desired product (2.5 g, 96%) as a yellow solid: 387 [C15H20BrN3O4+H]+.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washThe solids were washed with aqueous ammonium chloride, brine and water

Sources & evidence

ORD record
ord-87225b570eb24fe9a4cb47d04930d254
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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