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

HRID 2035783Notes

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-208efd98e0eb4d69a111e5ee473dc66c
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575154B2

Reaction notes

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