Potassium Iodide → HCID 61956811, compound

HRID 2207075Notes

Reaction equation

HRID 2207075 reaction equation
[F:1][CH:2]([F:5])[CH2:3][NH2:4].Br[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[I-].[K+]>C(N(C(C)C)CC)(C)C>[F:1][CH:2]([F:5])[CH2:3][NH:4][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 68320Ethyl 3-bromopropionateHCID 1362742,2-Difluoroethanamine

Product 1

HCID 61956811HCID 61956811, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
100 °C

Procedure

2,2-difluoroethylamine (0.50 g) was added to a suspension of ethyl 3-bromopropanoate (1.1 g), potassium iodide (0.10 g) in diisopropylethylamine (1.2 mL) and the mixture was stirred at 100° C. for 3.5 h. The mixture was cooled to RT and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford the sub-title compound (0.69 g) as a pale yellow oil; 1H NMR (300 MHz, CDCl3); 5.81 (1H, tt), 4.13 (2H, q), 2.95 (2H, dt), 2.93 (2H, t), 2.48 (2H, t), 1.24 (3H, t).

Workup

  1. temperatureThe mixture was cooled to RT
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-0c7ac186ad9c4fd7b07bd9bf06625fce
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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