Boron tribromide → HCID 178434358, compound

HRID 392223Notes

Reaction equation

HRID 392223 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>ClCCl>[OH: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

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178487565HCID 178487565, compound

Product 1

HCID 178434358HCID 178434358, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-methoxy-3-methyl-1H-indazole (2.0 g, Reference Example 49) in dichloromethane (75 ml) was cooled to 0° C. then treated with a solution of boron tribromide in dichloromethane (54 ml, 1M). The mixture was allowed to warm to room temperature and then stirred for 12 hours. The solution was poured into an ice-saturated sodium bicarbonate mixture and the aqueous layer was extracted three times with ethyl acetate (50 ml). The combined extracts were dried over sodium sulphate then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (2:1, v/v) to yield the title compound (1.7 g).

Workup

  1. extractionthe aqueous layer was extracted three times with ethyl acetate (50 ml)
  2. dry with materialThe combined extracts were dried over sodium sulphate
  3. customthen evaporated
  4. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (2:1

Sources & evidence

ORD record
ord-bc0013f07a0f4f04983a8a187a3013a2
Source dataset
uspto-grants-2004_10
Patent number
US06800645B1

Reaction notes

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