Sodium Chloride → HCID 90017318, compound

HRID 1054997Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

2-Chloro-6-methyl-3-(trifluoromethyl)pyridine (200 mg, 1.02 mmol, Eq: 1.00), (4-methoxyphenyl)methylamine (168 mg, 159 μL, 1.23 mmol, Eq: 1.2) and potassium carbonate (212 mg, 1.53 mmol, Eq: 1.5) were combined in dimethylformamide (1.2 mL) to give a light yellow suspension. The mixture was stirred at 120° C. for 2 h. Additional potassium carbonate (141 mg, 1.02 mmol, Eq: 1) and (4-methoxyphenyl)methanamine (140 mg, 133 μL, 1.02 mmol, Eq: 1) were added and the mixture was stirred at 120° C. for 7 h. Saturated aqueous sodium chloride solution was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to an oil. The product (100 mg, 33%) was obtained as a colorless oil by column chromatography (SiO2, ethyl acetate/n-heptane). MS: m/z=297.3 (M+H+)

Workup

customto give a light yellow suspension
stirringthe mixture was stirred at 120° C. for 7 h
extractionthe mixture was extracted with ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated to an oil

Sources & evidence

ORD record: ord-14648523ceed49cdb7ba63ee5c513b60
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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