Azidotrimethylsilane → HCID 178487641, compound

HRID 915905Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7](/[CH:9]=[CH:10]\[N+:11]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.[Si]([N:24]=[N+:25]=[N-])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[N:24]=[N:25][NH:11][CH:10]=2)[CH:6]=[CH:5][C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 2-{2-methoxy4-[(Z)-2-nitroethenyl]phenyl}pyridine (0.23 g, 0.89 mmol) and TMSN3 (0.18 mL, 1.34 mmol) in DMF (1 mL) was heated to slowly to 50° C. while TBAF (0.98 mL, 1.0 M in THF, 0.98 mol) was added dropwise over 20 min. The resulting reaction mixture was continued to stir at 50° C. for 30 min. The mixture was partitioned between sat. NaHCO3 (20 mL) and EtOAc (60 mL). The phases were separated and the aqueous layer was extracted with EtOAc (3×60 mL). The combined organic layers were dried (MgSO4), filtered and concentrated. The residue was purified on silica gel (20:1 hexane-ethyl acetate) to afford a yellow solid.

Workup

additionwas added dropwise over 20 min
customThe resulting reaction mixture
customThe mixture was partitioned between sat. NaHCO3 (20 mL) and EtOAc (60 mL)
customThe phases were separated
extractionthe aqueous layer was extracted with EtOAc (3×60 mL)
dry with materialThe combined organic layers were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified on silica gel (20:1 hexane-ethyl acetate)
customto afford a yellow solid

Sources & evidence

ORD record: ord-d71f459474f448798b53a85f4873100b
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268151B2

Reaction notes

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