Anisole → 4-(5-(pyridin-4-yl)-1H-imidazol-1-yl)phenol

HRID 33940Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[CH:18][N:17]=[CH:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[N:23]1[CH:24]=[CH:25][C:20]([C:19]2[N:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=3)[CH:16]=[N:17][CH:18]=2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of Preparation 81 (4-(1-(4-(benzyloxy)phenyl)-1H-imidazol-5-yl)pyridine, 2 g, 6.1 mmol) and anisole (13 mL, 122 mmol) in trifluoracetic acid (50 mL) was heated at 75° C. for 24 h. The solvent was removed in vacuo and the residue was purified via silica gel chromatography with chloroform-methanol-ammonium hydroxide (94:5:1) to afford 1.27 g (88%) of the title compound; diagnostic 13C NMR signals (100 MHz, CDCl3) δ 158.402, 149.145, 141.061, 138.018, 120.600, 129.822, 127.482, 127.370, 121.933, 116.497; MS (AP/Cl) 238.3 (M+H)+.

Workup

customThe solvent was removed in vacuo
customthe residue was purified via silica gel chromatography with chloroform-methanol-ammonium hydroxide (94:5:1)

Sources & evidence

ORD record: ord-3e6267a3b3f14bc9ad984630943ff306
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429665B2

Reaction notes

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