Ethyl Acetate → HCID 59203837, compound

HRID 2241825Notes

Reaction equation

HRID 2241825 reaction equation
C[O:2][C:3]1[CH:18]=[CH:17][C:6]2[N:7]=[C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH2:16])=[N:14][CH:15]=3)[O:9][C:5]=2[CH:4]=1.B(Br)(Br)Br.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[NH2:16][C:13]1[N:14]=[CH:15][C:10]([C:8]2[O:9][C:5]3[CH:4]=[C:3]([OH:2])[CH:18]=[CH:17][C:6]=3[N:7]=2)=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 24780799HCID 24780799, compound

Product 1

HCID 59203837HCID 59203837, compoundYield 116.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a stirred and cooled (ice bath) solution of 5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-amine (2.07 mmol) in CH2Cl2 (50 mL) was slowly added boron tribromide 1M in CH2Cl2 (4.15 mL) from a pressure equalized dropping funnel. After full addition the reaction mixture was stirred 5 mins in the ice bath, before it was allowed to reach room temperature and then stirred at room temperature overnight. The reaction mixture was cooled (ice bath) and diluted with CH2Cl2 (100 mL), followed by EtOAc (100 mL), water (100 mL) and sat aq NaHCO3 (100 mL) and the resulting mixture allowed to reach room temperature and stirred vigorously for 10 mins. The organic layer was separated and the aqueous layer extracted with CH2Cl2 (3×100 mL), the combined organic layers were dried (Na2SO4), filtered and evaporated to give 0.55 g of 2-(6-aminopyridin-3-yl)-1,3-benzoxazol-6-ol, as a pale yellow foamy solid. MS m/z 228 (M+H).

Workup

  1. additionAfter full addition the reaction mixture
  2. customto reach room temperature
  3. stirringstirred at room temperature overnight
  4. temperatureThe reaction mixture was cooled (ice bath)
  5. customto reach room temperature
  6. stirringstirred vigorously for 10 mins
  7. customThe organic layer was separated
  8. extractionthe aqueous layer extracted with CH2Cl2 (3×100 mL)
  9. dry with materialthe combined organic layers were dried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-b7ee00d1b9974240a7b494ca2673d9c5
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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