Lithium Carbonate → 1-{2-Hydroxy-4-[3-(3-iodo-benzyl)-[1,2,4]oxadiazol-5-ylmethoxy]-3-methyl-phenyl}-ethanone

HRID 1161164Notes

Reaction equation

C(=O)([O-])[O-].[Li+].[Li+].Cl[CH2:8][C:9]1[O:13][N:12]=[C:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([I:21])[CH:16]=2)[N:10]=1.[OH:22][C:23]1[C:28]([CH3:29])=[C:27]([OH:30])[CH:26]=[CH:25][C:24]=1[C:31](=[O:33])[CH3:32].C1C2C(C3ON=C(N)N=3)CN(C2)C1>CN(C)C=O.O>[OH:22][C:23]1[C:28]([CH3:29])=[C:27]([O:30][CH2:8][C:9]2[O:13][N:12]=[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([I:21])[CH:16]=3)[N:10]=2)[CH:26]=[CH:25][C:24]=1[C:31](=[O:33])[CH3:32]

Participants

Conditions

Temperature: 60 °C

Procedure

Add lithium carbonate (49 mg, 0.66 mmol) and 5-chloromethyl-3-(3-iodo-benzyl)-[1,2,4]oxadiazole (200 mg, 0.60 mmol) to a solution of 1-(2,4-dihydroxy-3-methyl-phenyl)-ethanone (110 mg, 0.66 mmol) in anhydrous dimethylformamide (20 mL) 4]oxadiazole (200 mg, 0.60 mmol). Heat the reaction mixture at 60° C. overnight. Cool the reaction mixture to RT, pour into H2O, and extract with diethyl ether (3×). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate to provide the title compound (150 mg). LC-MS (m/e): 463 (M−1).

Workup

temperatureCool the reaction mixture to RT
extractionextract with diethyl ether (3×)
washCombine the organic layers, wash with brine
dry with materialdry over sodium sulfate
concentrationconcentrate

Sources & evidence

ORD record: ord-c814fed80f374eaa9ec6e4f4ef97c3c8
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816523B2

Reaction notes

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