Boron tribromide → HCID 178434358, compound

HRID 1880392Notes

Reaction equation

HRID 1880392 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:12])=[N:8][NH:9]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:12][C:7]1[C:6]2[C:10](=[CH:11][C:3]([OH:2])=[CH:4][CH:5]=2)[NH:9][N:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178487565HCID 178487565, compound

Product 1

HCID 178434358HCID 178434358, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cold solution of 6-methoxy-3-methyl-1H-indazole (620 mg, 3.82 mmol) in CH2Cl2 (25 mL) was added a solution of BBr3 in CH2Cl2 (1 M, 17 mL). The ice bath was removed and the reaction was allowed to warm to room temperature and stirred overnight. The solution was carefully quenched by slowly pouring into iced saturated aqueous NaHCO3. The phases were separated and the aqueous phase was extracted with EtOAc (3×). The combined organic extracts were concentrated and the crude material was purified Biotage (40S column, 45-60% acetone/heptane) to provide 3-methyl-1H-indazol-6-ol (458 mg, 81%).

Workup

  1. customThe ice bath was removed
  2. customThe solution was carefully quenched
  3. additionby slowly pouring into iced saturated aqueous NaHCO3
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with EtOAc (3×)
  6. concentrationThe combined organic extracts were concentrated
  7. customthe crude material was purified Biotage (40S column, 45-60% acetone/heptane)

Sources & evidence

ORD record
ord-786c68f3bff64acaa938ad6cc0f95434
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

Loading…