3-Fluorobenzylamine → HCID 86664548, compound

HRID 513288Notes

Reaction equation

HRID 513288 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([Cl:13])[C:3]=1[Cl:14].[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH2:20].CCN(C(C)C)C(C)C>C(C#N)(C)=O>[Cl:14][C:3]1[C:4]([Cl:13])=[N:5][CH:6]=[C:7]([C:2]=1[NH:20][CH2:19][C:18]1[CH:21]=[CH:22][CH:23]=[C:16]([F:15])[CH:17]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 668533-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 79611304,5,6-Trichloronicotinic acid ethyl ester

Product 1

HCID 86664548HCID 86664548, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 4,5,6-trichloronicotinate (200 mg, 0.78 mmol) in AcCN (1.5 mL) was added 3-fluorobenzylamine (0.108 mL, 0.94 mmol) and DIPEA (0.167 mL, 0.94 mmol). The mixture was stirred at room temperature for 5 h them at 50° C. until the reaction is over. The solution was cooled and concentrated, the resulting residue was diluted with water, the solid was then collected by filtration to give ethyl 5,6-dichloro-4-(3-fluorobenzylamino)nicotinate (260 mg).

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated
  3. additionthe resulting residue was diluted with water
  4. filtrationthe solid was then collected by filtration

Sources & evidence

ORD record
ord-669a8ed46d5f43fa8b43cdf0ee69a91d
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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