2-Chloro-4-iodo-5-(trifluoromethyl)pyridine → 2-Chloro-5-(trifluoromethyl)-4-pyridinamine

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH3:13].CO>>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:13])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1

Participants

Reactant 2

HCID 27737912-Chloro-4-iodo-5-(trifluoromethyl)pyridine

HCID 21705897Ammonia methanol

Product 1

HCID 713061562-Chloro-5-(trifluoromethyl)-4-pyridinamine

Conditions

Temperature: 130 °C

Procedure

2-chloro-4-iodo-5-(trifluoromethyl)pyridine was dissolved in 7 M Ammonia/Methanol. It was heated in a Biotage Initiator microwave synthesizer at 130° C. for 1 h. A mixture of the 2- and 4-substituted products was obtained. The solvent was removed and the residue was purified by silica gel chromatography (DCM/MeOH) gradient. The pure title compound was isolated.

Workup

additionA mixture of the 2-
custom4-substituted products was obtained
customThe solvent was removed
customthe residue was purified by silica gel chromatography (DCM/MeOH) gradient

Sources & evidence

ORD record: ord-9b41f0139f354fb48a2eae08892cfa9a
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501763B2

Reaction notes

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