Triethylamine → N-(3,4-dimethoxybenzyl)-4-iodo-6-(trifluoromethyl)pyridin-2-amine

HRID 69961Notes

Reaction equation

HRID 69961 reaction equation
Cl[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17](NC=O)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].C[CH2:27][N:28](CC)CC>CN1C(=O)CCC1>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:27][NH:28][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108597852-Chloro-4-iodo-6-(trifluoromethyl)pyridineHCID 15534909N-(3,4-Dimethoxyphenyl)formamide

Product 1

HCID 69047366N-(3,4-dimethoxybenzyl)-4-iodo-6-(trifluoromethyl)pyridin-2-amineYield 36%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-chloro-4-iodo-6-(trifluoromethyl)pyridine (1.0 equiv.), (3,4-dimethoxyphenyl)methanamide (5.0 equiv.), and Et3N (5.0 equiv.) in NMP (0.7M) was microwaved to 100° C. for 10 min. The solution was directly purified via reverse phase HPLC, the pure fractions were neutralized with solid NaHCO3, extracted with EtOAc, dried with MgSO4, and concentrated to give N-(3,4-dimethoxybenzyl)-4-iodo-6-(trifluoromethyl)pyridin-2-amine in 36% yield. LCMS (m/z): 347.1 (MH+); LC Rt=3.96 min.

Workup

  1. customThe solution was directly purified via reverse phase HPLC
  2. extractionextracted with EtOAc
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9d2b526ee3c94aabbfcba7cb1984396f
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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