Boron tribromide → HCID 19761451, compound

HRID 373841Notes

Reaction equation

HRID 373841 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:17]C)[CH:14]=2)[NH:9]1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:17])[CH:14]=2)[NH:9]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19761442HCID 19761442, compound

Product 1

HCID 19761451HCID 19761451, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.25 g 2-(2-aminophenyl)-5-methoxy-2,3-dihydro-1H-indole in 115 ml CH2Cl2 was added dropwise to 90.4 ml 1.0M BBr3 in CH2Cl2 at 0° C. The solution was stirred at 0°-5° C. for one hour, and then quenched by dropwise addition of 135 ml water. A total of 400 ml 7.5% NaHCO3 was added dropwise, and the resulting solution was stirred 30 minutes. It was then basified to a pH of ~9 with K2CO3 and extracted with EtOAc. The extracts were washed with saturated NaCl solution, dried (MgSO4), and concentrated to yield 5.10 g solid. Trituration with 5% EtOAc/CH2Cl2 and recrystallization from MeOH/water yielded 1.00 g solid, m.p. 169°-171° C.

Workup

  1. customquenched by dropwise addition of 135 ml water
  2. additionA total of 400 ml 7.5% NaHCO3 was added dropwise
  3. stirringthe resulting solution was stirred 30 minutes
  4. extractionextracted with EtOAc
  5. washThe extracts were washed with saturated NaCl solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ee07aef651894cb19e25a924e0d825d0
Source dataset
uspto-grants-1992_11
Patent number
US05166170

Reaction notes

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