Potassium Carbonate → HCID 86711921, compound

HRID 1475228Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[CH3:7][C:8]1[NH:12][N:11]=[C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[N:14]=2)[N:9]=1.Br[CH2:30][C:31]1[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=1>C1COCC1>[CH3:7][C:8]1[N:12]([CH2:30][C:31]2[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=2)[N:11]=[C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([O:24][C:25]([F:28])([F:26])[F:27])=[CH:22][CH:23]=3)[N:14]=2)[N:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of K2CO3 (2.63 g, 19.0 mmol), 5-(5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (Intermediate B, 3.70 g, 11.9 mmol) and 3-(bromomethyl)phenol (1.78 g, 9.52 mmol) was dissolved in THF (48 mL) and stirred at 50° C. for 16 h. The reaction mixture was filtered, the solvent was removed under reduced pressure, and the residue was purified by silica gel chromatography (0% to 80% EtOAc in Hexanes) to afford the title compound. MS (ES+) C19H14F3N5O3 requires: 417. found 418 [M+H]+; 1H-NMR (600 MHz, CD3OD) δ ppm 8.22 (d, J=8.8 Hz, 2H), 7.61 (d, J=8.0 Hz, 2H), 7.19 (d, J=7.8 Hz 1H), 6.72 (m, 2H), 6.67 (s, 1H), 5.49 (s, 2H), 2.56 (s, 3H).

Workup

filtrationThe reaction mixture was filtered
customthe solvent was removed under reduced pressure
customthe residue was purified by silica gel chromatography (0% to 80% EtOAc in Hexanes)

Sources & evidence

ORD record: ord-943529e4ab104f89be4ce226e8d7d29e
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018380B2

Reaction notes

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