Diisopropylethylamine → HCID 71116560, compound

HRID 1051498Notes

Reaction equation

HRID 1051498 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[NH2:12][CH:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1.CCN(C(C)C)C(C)C>CS(C)=O.O.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:12][CH:13]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]2)[CH:3]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 27563701-Boc-3-aminopyrrolidineHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 71116560HCID 71116560, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-fluoro-1-nitrobenzene (500 mg, 2.27 mmol) and tert-butyl 3-aminopyrrolidine-1-carboxylate (390 mg, 2.27 mmol) in DMSO (5 mL) was added DIPEA (351 mg, 2.72 mmol) and the solution stirred in a sealed bottle at room temperature for 16 h. After LCMS analysis indicated completion of the reaction, the solution was diluted with water (100 mL) and DCM (100 mL). The organic layer was washed by water (30 mL×2) and brine (30 mL) and dried over anhydrous Na2SO4 before being filtered and concentrated to yield the desired product (670 mg Yield 80%). The material was used in the next step without further purification. LCMS (m/z): 386.1 (M+1).

Workup

  1. customcompletion of the reaction
  2. washThe organic layer was washed by water (30 mL×2) and brine (30 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationbefore being filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a08d355f0b2340c9a21ff958e872d7b6
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

Loading…