Azidotrimethylsilane → (5-azido-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol

HRID 455592Notes

Reaction equation

HRID 455592 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:15]3([CH2:17][O:16]3)[C:14]3[CH:13]=[C:12]([Cl:18])[N:11]=[C:10]([F:19])[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.[N:20]([Si](C)(C)C)=[N+:21]=[N-:22]>CN(C=O)C.CCOC(C)=O.O>[N:20]([C:15]1([CH2:17][OH:16])[C:14]2[CH:13]=[C:12]([Cl:18])[N:11]=[C:10]([F:19])[C:9]=2[O:8][C:5]2[C:4]1=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[N+:21]=[N-:22]

Participants

6

Reactant 2

HCID 78378Azidotrimethylsilane2×HCID 866583687-Bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,2'-oxirane]

Product 1

HCID 86658369(5-azido-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanolYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,2′-oxirane] (23.5 g, 68.6 mmol) in DMF (600 mL) was added azidotrimethylsilane (54.6 mL, 412 mmol). The reaction mixture was stirred at RT for 6 hours. Additional azidotrimethylsilane (54.6 mL, 412 mmol) was added and the reaction was stirred at RT for 18 hours. The reaction mixture was diluted with EtOAc and water. The organic layer was separated, washed sequentially with a saturated aqueous LiCl solution and brine before drying over sodium sulfate. The solution was concentrated under reduced pressure to afford (5-azido-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol (26.12 g, 67.7 mmol, 99% yield).

Workup

  1. stirringthe reaction was stirred at RT for 18 hours
  2. customThe organic layer was separated
  3. washwashed sequentially with a saturated aqueous LiCl solution and brine
  4. dry with materialbefore drying over sodium sulfate
  5. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fe65a7638c71404ebbcdab8340b98396
Source dataset
uspto-grants-2013_07
Patent number
US08497264B2

Reaction notes

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