Boron tribromide → HCID 10662673, compound

HRID 1901790Notes

Reaction equation

HRID 1901790 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([CH3:19])=[C:6]2[CH2:20][C:21]([NH:23][NH2:24])=[O:22].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([CH3:19])=[C:6]2[CH2:20][C:21]([NH:23][NH2:24])=[O:22]

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 10687376HCID 10687376, compound

Product 1

HCID 10662673HCID 10662673, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 165 mg (0.51 mmol) of 5-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide (Example 17, Part B) in 30 mL of CH2Cl2 was added 1.0 mL of 1M BBr3 in CH2Cl2 and the mixture stirred for 1.5 hours, then an addition 0.5 mL of the BBr3 solution was added. After 1.5 hours, the reaction mixture was washed with Na2CO3 solution, dried (Na2SO4), and concentrated at reduce pressure. The residue was chromatographed on silica eluting with 2% MeOH/CH2Cl2 →5% MeOH/CH2Cl2 to give 60 mg (39% yield) of 5-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide, mp, 216°-219° C.

Workup

  1. additionwas added
  2. waitAfter 1.5 hours
  3. washthe reaction mixture was washed with Na2CO3 solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica eluting with 2% MeOH/CH2Cl2 →5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-d4c5c714f2d74a46b8ce6154598e7343
Source dataset
uspto-grants-1996_11
Patent number
US05578634

Reaction notes

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