Methyl Ethyl Ketone → N-(3,5-Bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide

HRID 1835307Notes

Reaction equation

[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12](Cl)=[N:11][CH:10]=1.CC(=O)CC.[IH:39].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([I:39])=[N:11][CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1.00 g (2.05 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-chloro-N-methyl-4-o-tolyl-nicotinamide in 10 ml 2-butanone 1.1 g (7.2 mmol) sodium iodide and 0.28 ml (2.1 mmol) hydroiodic acid (57% in water) were added at room temperature. The mixture was heated at 80° C. for 2 h. After cooling to room temperature the mixture was diluted with ethyl acetate and treated with saturated aqueous sodium bicarbonate solution. The layers were separated, the organic layer washed with water, dried with magnesium sulfate and concentrated to give 1.5 g of crude product. Flash column chromatography gave 1.11 g (93.6%) of the title compound as a yellow oil.

Workup

temperatureAfter cooling to room temperature the mixture
customThe layers were separated
washthe organic layer washed with water
dry with materialdried with magnesium sulfate
concentrationconcentrated
customto give 1.5 g of crude product

Sources & evidence

ORD record: ord-11579c28d0c14b62b6039679728b6de9
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770637B2

Reaction notes

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