Ethanol → Methyl 5-chloro-6-[(3,4-dimethoxybenzyl)amino]-2-(3-fluorophenyl)nicotinate

HRID 717827Notes

Reaction equation

HRID 717827 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(O)C.[CH2:23]([NH2:34])[C:24]1[CH:33]=[CH:32][C:29]([O:30][CH3:31])=[C:26]([O:27][CH3:28])[CH:25]=1>>[Cl:1][C:2]1[C:3]([NH:34][CH2:23][C:24]2[CH:33]=[CH:32][C:29]([O:30][CH3:31])=[C:26]([O:27][CH3:28])[CH:25]=2)=[N:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 3

HCID 702EthanolHCID 79832VeratrylamineHCID 58515941Methyl 5,6-dichloro-2-(3-fluorophenyl)nicotinate

Product 1

HCID 66993070Methyl 5-chloro-6-[(3,4-dimethoxybenzyl)amino]-2-(3-fluorophenyl)nicotinateYield 82.5%

Procedure

A solution of methyl 5,6-dichloro-2-(3-fluorophenyl)nicotinate (55 mg, 0.18 mmol) in ethanol (1 mL, 20 mmol) was treated with veratrylamine (82 μL, 0.55 mmol) and refluxed for 30 minutes. The reaction mixture was concentrated and purified by flash column chromatography using ethyl acetate in hexanes (0-30%) to give the desired product (64 mg, 81%). LCMS calculated for C22H21ClFN2O4 (M+H)+: m/z=431.1. found: 430.9.

Workup

  1. temperaturerefluxed for 30 minutes
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-11cf681f0759493aa6aca396954f5f92
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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