p-Toluenesulfonyl azide → HCID 86662263, compound

HRID 1627402Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:14]=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:23][CH3:24].[Li]CCCC.S([N:40]=[N+:41]=[N-:42])(C1C=CC(C)=CC=1)(=O)=O>C1COCC1>[N:40]([C:14]1[N:15]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[C:11]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:23][CH3:24])[CH:4]=2)([CH3:9])[CH3:10])=[CH:12][N:13]=1)=[N+:41]=[N-:42]

Participants

Conditions

Temperature: -78 °C

Procedure

To a −78° C. solution of 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (0.215 g, 0.62 mmol) in 3 mL of THF (3 mL) was added 1.67 M BuLi (0.45 mL, 0.75 mmol). The reaction was stirred at −78° C. for 30 min and then tosyl azide (0.160 g, 0.81 mmol) in THF (0.5 mL) was added dropwise. The reaction was stirred at −78° C. for 1 h when it was determined to be complete by LCMS. The reaction was quenched at −78° C. with pH 7 buffer and allowed to warm to room temperature. The mixture was extracted with DCM (3×10 mL) and dried with MgSO4. The residue was purified by column chromatography using Hex:EtOAc as eluents to afford 2-azido-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (131 mg) as a yellow oil. MS (EI) m/z 386 [M+H]+.

Workup

stirringThe reaction was stirred at −78° C. for 1 h when it
customThe reaction was quenched at −78° C. with pH 7 buffer
temperatureto warm to room temperature
extractionThe mixture was extracted with DCM (3×10 mL)
dry with materialdried with MgSO4
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-275212631a024b15a4181772e6378413
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785488B2

Reaction notes

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