Water → (1H-Imidazol-4-yl)-(6-methoxynaphthalen-2-yl)-(pyridin-3-yl)methanol

HRID 1368514Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([C:25]([C:27]1[N:28]=[CH:29][N:30](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:31]=1)=[O:26])[CH:19]=[CH:18]2.O>CCOCC.CCCCCC.C1COCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[NH:30]1[CH:31]=[C:27]([C:25]([C:20]2[CH:19]=[CH:18][C:17]3[C:22](=[CH:23][CH:24]=[C:15]([O:14][CH3:13])[CH:16]=3)[CH:21]=2)([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[OH:26])[N:28]=[CH:29]1

Participants

Conditions

Temperature: -78 °C

Procedure

3-Bromopyridine (0.92 ml) was dissolved in ether (20 ml), and the solution was cooled at −78° C. To the solution was slowly added dropwise a solution of n-butyllithium in hexane (1.6 M 5.9 ml), the mixture was stirred for 20 min at −78° C. To the reaction mixture was slowly added a solution of (6-methoxynaphthalen-2-yl)-(1-trityl-1H-imidazol-4-yl)ketone (1.0 g) in THF (8 ml), and the mixture was stirred for 30 min at −78° C. To the reaction mixture was added water, and mixture was diluted with 2% citric acid (50 ml). The dilution was extracted with ethyl acetate, washed with saturated aqueous solution of sodium chloride, dried and concentrated. The residue was recrystallized from a mixed solution of ethyl acetate and diethyl ether to give the titled compound (0.98 g) as a pale yellow powder.

Workup

stirringthe mixture was stirred for 30 min at −78° C
extractionThe dilution was extracted with ethyl acetate
washwashed with saturated aqueous solution of sodium chloride
customdried
concentrationconcentrated
customThe residue was recrystallized from a mixed solution of ethyl acetate and diethyl ether

Sources & evidence

ORD record: ord-0516e1c17bff44d1ab92f511b49160f9
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573289B1

Reaction notes

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