Tetrahydrofuran → 2,6-dichloro-N-(pyridin-3-ylmethyl)pyridine-3-carboxamide

HRID 547501Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C1COCC1.[NH2:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.CCN(C(C)C)C(C)C>CCOC(C)=O>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:6]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of acid 2,6-dichloronicotinic acid (19.2 g, 0.1 mol), N,N′-carbonyldiimidazole (CDI, 17.8 g, 0.11 mmol) and THF (1 L) was stirred at 60° C. for 30 min and cooled to room temperature. To the mixture was added 3-aminomethylpyridine (10.2 mL, 0.1 mol) and DIEA (21 mL, 0.12 mol). The reaction mixture was stirred at room temperature for 4 hrs, and diluted with EtOAc. The organic layer was washed with H2O, brine, dried over Na2SO4. Concentration of the organic solution gave the 2,6-dichloro-N-(pyridin-3-ylmethyl)nicotinamide (20.5 g, 73%). LRMS (M+H+) m/z 282.0; (M+2+H+) m/z 283.9.

Workup

temperaturecooled to room temperature
stirringThe reaction mixture was stirred at room temperature for 4 hrs
washThe organic layer was washed with H2O, brine
dry with materialdried over Na2SO4

Sources & evidence

ORD record: ord-a9cb3e64747b48728a80dd7579a42f5e
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939548B2

Reaction notes

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