Boron tribromide → HCID 136358478, compound

HRID 1295046Notes

Reaction equation

HRID 1295046 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[C:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:24][CH2:25][CH3:26])[N:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[C:18]1([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:12]=2[N:11]([CH2:24][CH2:25][CH3:26])[N:10]=[C:9]3[C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68883946HCID 68883946, compound

Product 1

HCID 136358478HCID 136358478, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-methoxyphenyl)-7-phenyl-1-propyl-1H-indazole (0.375 g, 1.09 mmol) in CH2Cl2 (15 mL) was added BBr3 (0.207 mL, 2.19 mmol) at −78° C. The solution was stirred for 15 minutes and allowed to stand overnight in the refrigerator. The reaction was quenched with NH4OH (20 mL) and extracted with CH2Cl2. The organic layer was washed with water and dried (MgSO4). The reaction was purified by flash chromatography (5/1 hexane/ethyl acetate) to give the title compound as a white solid (0.147 g, 0.45 mmol, 41%).

Workup

  1. waitto stand overnight in the refrigerator
  2. customThe reaction was quenched with NH4OH (20 mL)
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customThe reaction was purified by flash chromatography (5/1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fe8849fc394e4125a4ff6c3ce6201747
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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