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

HRID 931610
Notes
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Reaction equation

HRID 931610 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 67382689ethyl 2-(3-bromo-5-hydroxy-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate

Product 1

HCID 86761966ethyl 2-(5-azido-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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

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

Sources & evidence

ORD record
ord-8646420b01224dbaa167d5113c1e2357
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296759B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes