Bicarbonate Ion → HCID 86761964, compound

HRID 931591Notes

Reaction equation

HRID 931591 reaction equation
[N:1]([Si](C)(C)C)=[N+:2]=[N-:3].B(F)(F)F.CCOCC.[Br:17][C:18]1[CH:19]=[C:20]2[C:30](=[CH:31][CH:32]=1)[O:29][C:23]1[CH:24]=[N:25][C:26]([Cl:28])=[CH:27][C:22]=1[C:21]2([CH:34]([CH3:37])[CH2:35][OH:36])O.C(=O)(O)[O-]>C1COCC1.CCOC(C)=O>[N:1]([C:21]1([CH:34]([CH3:37])[CH2:35][OH:36])[C:22]2[CH:27]=[C:26]([Cl:28])[N:25]=[CH:24][C:23]=2[O:29][C:30]2[C:20]1=[CH:19][C:18]([Br:17])=[CH:32][CH:31]=2)=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 769Bicarbonate IonHCID 8000Boron trifluoride etherate3×HCID 78378Azidotrimethylsilane3×HCID 86761962HCID 86761962, compound

Product 1

HCID 86761964HCID 86761964, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
66 °C

Procedure

Azidotrimethylsilane (1.432 mL, 10.79 mmol) and borontriflouride etherate (1.368 mL, 10.79 mmol) were added sequentially to a solution of 7-bromo-3-chloro-5-(1-hydroxypropan-2-yl)-5H-chromeno[2,3-c]pyridin-5-ol (2000 mg, 5.40 mmol) in THF (50 mL). The reaction mixture was heated to 66° C. After 12 h reaction time, additional azidotrimethylsilane (1.432 mL, 10.79 mmol) and borontriflouride etherate (1.368 mL, 10.79 mmol) were added and the reaction mixture was continued to be heated to 65° C. After 24 h reaction time, additional azidotrimethylsilane (1.432 mL, 10.79 mmol) and borontriflouride etherate (1.368 mL, 10.79 mmol) were added and the reaction mixture was continued to be heated to 65° C. After 32 h reaction time, the reaction mixture was cooled to rt and aqueous saturated bicarbonate solution was added carefully, followed by EtOAc. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (10-55% EtOAc/hexanes). 2-(5-azido-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)propan-1-ol (1.32 g, 85% purity) was isolated of a white solid and taken onto the next step without further purification.

Workup

  1. additionwere added
  2. temperatureto be heated to 65° C
  3. additionwere added
  4. temperatureto be heated to 65° C
  5. customAfter 32 h reaction time
  6. temperaturethe reaction mixture was cooled to rt
  7. customThe organic phase was separated
  8. dry with materialdried over MgSO4
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified by flash chromatography (10-55% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6a05a4c07ce043f4b8b6b353621a7d34
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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