Diisopropylethylamine → HCID 59233161, compound

HRID 1925114Notes

Reaction equation

HRID 1925114 reaction equation
Br.[Cl:2][C:3]1[N:8]=[N:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14](F)[CH:13]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[C:16]([NH:10][CH2:9][C:6]2[N:7]=[N:8][C:3]([Cl:2])=[CH:4][CH:5]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27833624-Bromo-2-fluoro-1-nitrobenzeneHCID 86639818HCID 86639818, compound

Product 1

HCID 59233161HCID 59233161, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound 10C (1.00 g, 4.46 mmol) and 4-bromo-2-fluoro-1-nitro-benzene (10D) (0.97 g, 4.40 mmol) in DMF (50 mL) with DIEA (1.30 g, 10 mmol) was stirred at 65° C. for two hours. The reaction was poured into ice/water and the solid precipitate was collected by filtration, washed with water and dried in vacuum over P2O5 overnight to give 1.5 g of desired product (10E). ESI-MS:m/z 342.9 (M+H)+.

Workup

  1. filtrationthe solid precipitate was collected by filtration
  2. washwashed with water
  3. dry with materialdried in vacuum over P2O5 overnight

Sources & evidence

ORD record
ord-8729b6579c82460b9de3c605fc05ffe2
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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