3,3,3-Trifluoropropylamine → HCID 86675154, compound

HRID 587690Notes

Reaction equation

HRID 587690 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:23]([F:26])([F:25])[F:24])/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[C:18](=O)[CH2:17][CH2:16]3)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].[F:27][C:28]([F:33])([F:32])[CH2:29][CH2:30][NH2:31].[BH3-]C#N.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:23]([F:26])([F:25])[F:24])/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[CH:18]([NH:31][CH2:30][CH2:29][C:28]([F:33])([F:32])[F:27])[CH2:17][CH2:16]3)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Participants

5

Reactant 3

HCID 100013,3,3-TrifluoropropylamineHCID 5003444Sodium cyanoborohydrideHCID 86675155HCID 86675155, compound

Product 1

HCID 86675154HCID 86675154, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a stirred solution of (E)-5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-2,3-dihydro-1H-inden-1-one (0.15 g, 0.35 mmol) in DCE (10 mL), was added trifluoropropyl amine (0.048 g, 0.42 mmol) and NaBH3CN (0.055 g, 0.875 mmol) in cooling and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with DCE, was washed with water and brine and dried over anhydrous Na2SO4. Concentration under reduced pressure gave the crude compound, which was purified by flash column chromatography (SiO2, 100-200 mesh; 10-15% EtOAc in petroleum ether) to afford the title compound as a colorless gummy material (0.042 g, 24%): 1H NMR (400 MHz, CDCl3) δ 7.38-7.20 (m, 5H), 6.62 (d, J=16.0 Hz, 1H), 6.34 (dd, J=16.0, 8.0 Hz, 1H), 5.83 (br, 1H), 5.52 (m, 1H), 4.12 (m, 1H), 3.02 (m, 3H), 2.82 (m, 1H), 2.50 (m, 2H), 1.82 (m, 1H), 1.42 (m, 1H); ESIMS m/z 497.98 ([M−H]−); IR (thin film) 3027, 1654, 815 cm−1.

Workup

  1. temperaturein cooling
  2. washwas washed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationConcentration under reduced pressure
  5. customgave the crude compound, which
  6. customwas purified by flash column chromatography (SiO2, 100-200 mesh; 10-15% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-df3bb7d86c7d48f383da7d9f825d770b
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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