Ethylene carbonate → 2-[2-(4-Chloro-6-methoxy-pyridin-3-yl)-4-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-imidazol-1-yl]-ethanol

HRID 1629136Notes

Reaction equation

C1(=O)O[CH2:4][CH2:3][O:2]1.[Cl:7][C:8]1[C:13]([C:14]2[NH:15][CH:16]=[C:17]([C:19]3[N:20]([CH:24]([CH3:26])[CH3:25])[N:21]=[CH:22][N:23]=3)[N:18]=2)=[CH:12][N:11]=[C:10]([O:27][CH3:28])[CH:9]=1>C(Cl)Cl>[Cl:7][C:8]1[CH:9]=[C:10]([O:27][CH3:28])[N:11]=[CH:12][C:13]=1[C:14]1[N:15]([CH2:4][CH2:3][OH:2])[CH:16]=[C:17]([C:19]2[N:20]([CH:24]([CH3:25])[CH3:26])[N:21]=[CH:22][N:23]=2)[N:18]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To warmed ethylene carbonate (34 g) was added 4-chloro-5-[4-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-1H-imidazol-2-yl]-2-methoxy-pyridine (8.74 g, 27.4 mmol) and the mixture heated at 130° C. for 3 h. The cooled reaction mixture was diluted with DCM and loaded onto silica (150 g). The silica was washed with DCM then 5% methanol in DCM. Methanolic fractions were combined and concentrated in vacuo to give the title compound as a brown foam (7.52 g, 75%). LCMS RT=2.65, [M+H]+=363/365. 1H NMR 400 MHz (CDCl3) δ: 8.27 (1 H, s), 8.02 (1 H, s), 7.85 (1 H, s), 6.93 (1 H, s), 5.98-5.82 (1 H, m), 4.00 (5 H, m), 3.88 (2 H, t, J=5.11 Hz), 1.51 (6 H, d, J=6.62 Hz).

Workup

customThe cooled reaction mixture
washThe silica was washed with DCM
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1d8a73d21e844f068621d588097967a6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785626B2

Reaction notes

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