4-Methoxybenzylamine → Ethyl 4-(4-methoxybenzylamino)-6-chloropyridine-3-carboxylate

HRID 715087Notes

Reaction equation

HRID 715087 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.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1>CS(C)=O>[Cl:13][C:4]1[CH:3]=[C:2]([NH:21][CH2:20][C:19]2[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Product 1

HCID 89814202Ethyl 4-(4-methoxybenzylamino)-6-chloropyridine-3-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Stir a mixture of ethyl 4,6-dichloronicotinate (16 g, 73.1 mmol), (4-methoxybenzyl)amine (10 g, 73.1 mmol), and TEA (15.2 g, 146 mmol) in DMSO (150 mL) at RT overnight. Add EtOAc, wash with water (2×), then brine (1×), dry the organics over MgSO4 and concentrate to afford the title compound (21 g, 90%). 1H NMR (300 MHz, CDCl3): δ 8.62 (s, 1H), 8.39 (s, 1H), 7.16 (d, J=8.7 Hz, 2H), 6.85-6.80 (m, 2H), 6.49 (s, 1H), 4.33-4.25 (m, 4H), 3.77 (s, 3H), 1.31 (t, J=6.9 Hz, 3H).

Workup

  1. washAdd EtOAc, wash with water (2×)
  2. dry with materialbrine (1×), dry the organics over MgSO4
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-c21f564000774016a6b809aa64ca25ba
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

Loading…