Potassium Carbonate → Ethyl 6-chloro-4-(3-fluorophenethylamino)nicotinate

HRID 2074435Notes

Reaction equation

HRID 2074435 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])[CH:3]=1.[F:14][C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][NH2:23])[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:13][C:4]1[CH:3]=[C:2]([NH:23][CH2:22][CH2:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([F:14])[CH:16]=2)[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5339282-(3-Fluorophenyl)ethanamineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Product 1

HCID 59744990Ethyl 6-chloro-4-(3-fluorophenethylamino)nicotinateYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4,6-dichloronicotinate (2.2 g, 10.0 mmol) and 3-fluoro-phenylethylamine (1.5 g, 11.0 mmol) in DMF (20 mL) was added K2CO3 (4.1 g, 30 mmol) at r.t. The reaction mixture was stirred at r.t. overnight. The reaction mixture was filtered and concentrated under reduced pressure. The resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O to give ethyl 6-chloro-4-(3-fluorophenethylamino)nicotinate (1.1 mg, 34%). LRMS (M+H+) m/z 323.0.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified on RP-HPLC
  4. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-57fdaf224c514a94811519a63aa72785
Source dataset
uspto-grants-2011_04
Patent number
US07919511B2

Reaction notes

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