Azidotrimethylsilane → ethyl 2-(5-azido-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate

HRID 455618Notes

Reaction equation

[N:1]([Si](C)(C)C)=[N+:2]=[N-:3].[Br:8][C:9]1[CH:10]=[C:11]2[C:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])(O)[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([I:30])[CH:20]=3)[O:15][C:12]2=[N:13][CH:14]=1>C1(C)C=CC=CC=1>[N:1]([C:22]1([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:11]2[C:12](=[N:13][CH:14]=[C:9]([Br:8])[CH:10]=2)[O:15][C:16]2[C:21]1=[CH:20][C:19]([I:30])=[CH:18][CH:17]=2)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Azidotrimethylsilane (1.102 ml, 8.32 mmol) was added to a suspension of ethyl 2-(3-bromo-5-hydroxy-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate (2.33 g, 4.75 mmol) in toluene (31.7 ml). The reaction mixture was cooled to 0° C. and (diethyloxonio) trifluoroborate (0.753 ml, 5.94 mmol) was added slowly. The reaction mixture was allowed to warm to RT. After 30 min, the reaction mixture was quenched with MeOH (5 mL) followed by aqueous, saturated NaHCO3 solution (10 mL). The reaction mixture was extracted twice with EtOAc. The combined organic phases were washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to afford ethyl 2-(5-azido-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate as a yellow solid.

Workup

temperatureto warm to RT
customthe reaction mixture was quenched with MeOH (5 mL)
extractionThe reaction mixture was extracted twice with EtOAc
washThe combined organic phases were washed with brine
dry with materialdried over sodium sulfate
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-e2c4ccaaf64b49998a2d6333937c852e
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497264B2

Reaction notes

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