Boron tribromide → HCID 10475519, compound

HRID 1110018Notes

Reaction equation

HRID 1110018 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10]3=[C:11]([C:13]([CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][N:21]([C:24]5[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=5)[CH2:20][CH2:19]4)=[C:14]([CH3:15])[N:9]3[CH2:8][CH2:7][CH2:6]2)[CH:12]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10]3=[C:11]([C:13]([CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][N:21]([C:24]5[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=5)[CH2:20][CH2:19]4)=[C:14]([CH3:15])[N:9]3[CH2:8][CH2:7][CH2:6]2)[CH:12]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 10386517HCID 10386517, compound

Product 1

HCID 10475519HCID 10475519, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

7.9 g of 8-hydroxy-2-methyl-1-{2-[4-(4-methylpyridin-2-yl)piperazin-1-yl]ethyl}-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline (preparation see Example 5) were dissolved in 110 ml of dichloromethane. The solution was cooled to -10° C. A solution of 24.42 g of boron tribromide in 35 ml of dichloromethane was then added while the temperature was kept between -10° and 0° C. The mixture was allowed to react at about 0° C. for 30 minutes. To work up the reaction mixture it was added to a mixture of ice and saturated aqueous sodium bicarbonate solution. The organic phase was separated from the alkaline aqueous phase, washed until neutral, dried and evaporated. As a residue, 9.3 g of a pale grey, solid crude product remained, which was purified by chromatography on a small silica gel column. 4.4 g of cream-colored 8-hydroxy-2-methyl-1-{2-[4-(4-methylpyridin-2 -yl) piperazin-1-yl]ethyl}-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline having a melting point of 110° C. were obtained.

Workup

  1. customwas kept between -10° and 0° C
  2. customto react at about 0° C. for 30 minutes
  3. customThe organic phase was separated from the alkaline aqueous phase
  4. washwashed until neutral,
  5. customdried
  6. customevaporated
  7. customwhich was purified by chromatography on a small silica gel column

Sources & evidence

ORD record
ord-7704d291908645f68ff4df24fc2b590f
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

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