Ammonia → HCID 68282938, compound

HRID 1855305Notes

Reaction equation

HRID 1855305 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:19])=[CH:9][C:10]([O:17][CH3:18])=[CH:11][C:12]=3[CH:13]2Cl)=[CH:4][CH:3]=1.O1CCOCC1.[NH3:26]>>[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:19])=[CH:9][C:10]([O:17][CH3:18])=[CH:11][C:12]=3[CH:13]2[NH2:26])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 68282918HCID 68282918, compound

Product 1

HCID 68282938HCID 68282938, compound

Procedure

7-Bromo-9-chloro-4-fluoro-2-methoxy-9H-xanthene (45 g, 131 mmol) was dissolved in saturated solution ammonia in dioxane (1310 mL, 655 mmol) and stirred for 60 hrs at RT. The solution was concentrated in vacuo. The material was treated with saturated aqueous sodium carbonate and extracted into EtOAc. The organic extracts were concentrated. The product was purified from the concentrate via silica gel column chromatography (RediSep 330 g column) using 10-100% EtOAc in hexane to afford 7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-amine (10 g, 30:9 mmol).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionThe material was treated with saturated aqueous sodium carbonate
  3. extractionextracted into EtOAc
  4. concentrationThe organic extracts were concentrated
  5. customThe product was purified from the
  6. concentrationconcentrate via silica gel column chromatography (RediSep 330 g column)

Sources & evidence

ORD record
ord-66f9c4ad00924e46bc079c987fc9bce9
Source dataset
uspto-grants-2015_02
Patent number
US08962859B2

Reaction notes

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