Cuminol → 3-{[4-(1-Methylethyl)benzyl]oxy}pyridin-2-amine

HRID 1405696Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][OH:31])=[CH:26][CH:25]=1)([CH3:23])[CH3:22].Br[C:33]1[C:34]([NH2:39])=[N:35][CH:36]=[CH:37][CH:38]=1>C1(C)C=CC=CC=1.[Cl-].[Na+].O.[Cu]I>[CH3:22][CH:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][O:31][C:33]2[C:34]([NH2:39])=[N:35][CH:36]=[CH:37][CH:38]=2)=[CH:26][CH:25]=1)[CH3:23]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of cesium carbonate (2.82 g), 1,10-phenanthrolin (0.208 g), (4-isopropylphenyl)methanol (8.68 g), 3-bromopyridin-2-amine (1 g) and copper (I) iodide (0.110 g) in toluene (10 mL) was stirred under a nitrogen atmosphere at 110° C. overnight, and at 130° C. for 5 hr. The reaction mixture was added to saturated brine, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.92 g) as a pale-yellow solid.

Workup

waitat 130° C. for 5 hr
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-cf3476a2b0734bb5a6812b2c7b8db6de
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916551B2

Reaction notes

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