Diisopropylethylamine → HCID 24711068, compound

HRID 1894185Notes

Reaction equation

HRID 1894185 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.CC[N:14]([CH:18]([CH3:20])[CH3:19])C(C)C>CN1C(=O)CCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:9][C:4]2[CH:3]=[CH:2][CH:19]=[C:18]([NH2:14])[CH:20]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 24711068HCID 24711068, compoundYield 126.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromo-1-fluoro-2-nitro-benzene (1.14 ml, 9.25 mmol), benzene-1,3-diamiine (1.96 g, 18.1 mmol) and DIPEA (1.93 ml, 11.1 mmol) in dry NMP (5 ml) was deoxygenated by evacuate/fill N2 (×3), then stirred and heated at 120° C. under N2 for 18 hours. After cooling to RT the mixture was partitioned between EtOAc and 0.5N HCl. The organic layer was washed with H2O (×1), brine (×1) then dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica (10→40% EtOAc/petrol) to give the title compound (1.8 g) as a red solid. 1H NMR (400 MHz, DMSO-d6): 9.28 (1H, s), 8.20 (1H, d), 7.63 (1H, dd), 7.14 (1H, d), 7.07 (1H, t), 6.49 (1H, s), 6.48-6.39 (2H, m), 5.24 (2H, s).

Workup

  1. customwas deoxygenated
  2. customby evacuate/fill N2 (×3)
  3. temperatureAfter cooling to RT the mixture
  4. customwas partitioned between EtOAc and 0.5N HCl
  5. washThe organic layer was washed with H2O (×1), brine (×1)
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by chromatography on silica (10→40% EtOAc/petrol)

Sources & evidence

ORD record
ord-c88da455926147e587aee091f49b035e
Source dataset
uspto-grants-2013_08
Patent number
US08513276B2

Reaction notes

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