Triethylamine → HCID 86700479, compound

HRID 1404836Notes

Reaction equation

HRID 1404836 reaction equation
[F:1][C:2]1[C:8](F)=[C:7]([F:10])[CH:6]=[C:5]([N+:11]([O-:13])=[O:12])[C:3]=1[NH2:4].[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.CCN(CC)CC>CS(C)=O.II>[F:1][C:2]1[C:3]([NH2:4])=[C:5]([N+:11]([O-:13])=[O:12])[CH:6]=[C:7]([F:10])[C:8]=1[NH:20][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([F:14])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 27757632,3,4-Trifluoro-6-nitroaniline

Product 1

HCID 86700479HCID 86700479, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred suspension of compound 2 (0.060 g, 0.31 mmol, 1.0 equiv) in dry DMSO (0.3 mL) was added 4-fluorobenzylamine (0.117 g, 0.940 mmol, 3.00 equiv) followed by Et3N (54.0 μL, 0.370 mmol, 1.20 equiv) and I2 (catalytic, 1.0 mg). The reaction mixture was heated to 120° C. and stirred at 120° C. for 16 h. After consumption of the starting material (by TLC), the reaction mixture was cooled to RT, diluted with water (25 mL) and extracted with EtOAc (2×50 mL). The separated organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give crude; which was purified by silica gel column chromatography (EtOAc/Hexane 2:23) to afford compound 3 (0.064 g, 69%) as yellow solid. TLC: 25% EtOAc/Hexane (Rf: 0.20); 1H NMR (400 MHz, CDCl3): δ 7.67 (dd, J=2.0, 12.8 Hz, 1H), 7.31-7.28 (m, 2H), 7.05 (t, J=6.8 Hz, 2H), 6.05 (br s, 2H, Exc), 4.63 (d, J=6.0 Hz, 2H), 4.53 (br s, 1H, Exc); LC-MS: m/z=296 (M+-1) at RT 3.64 (98.8% purity)

Workup

  1. customAfter consumption of the starting material (by TLC)
  2. temperaturethe reaction mixture was cooled to RT
  3. additiondiluted with water (25 mL)
  4. extractionextracted with EtOAc (2×50 mL)
  5. dry with materialThe separated organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give crude
  9. customwhich was purified by silica gel column chromatography (EtOAc/Hexane 2:23)

Sources & evidence

ORD record
ord-cb57a936d3d1408d90646b4bdf21f995
Source dataset
uspto-grants-2014_12
Patent number
US08916133B2

Reaction notes

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