Boron tribromide → HCID 58504238, compound

HRID 2407717Notes

Reaction equation

HRID 2407717 reaction equation
C([O:8][CH2:9][C:10]1[S:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:13][N:14]=1)C1C=CC=CC=1.BrB(Br)Br>ClCCl>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:12]1[S:11][C:10]([CH2:9][OH:8])=[N:14][N:13]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58504217HCID 58504217, compound

Product 1

HCID 58504238HCID 58504238, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The compound prepared in Example 147 (0.295 g) was dissolved in dichloromethane (7 mL) and cooled to 0° C. Tribromoborane (0.3 mL) was added slowly and the reaction was allowed to warm and then was stirred overnight. The reaction was quenched with ethyl acetate/sodium hydrogen carbonate aqueous solution and the organic phase was washed with brine, dried over magnesium sulfate and filtered. The solution was concentrated and purified by column chromatography using an eluant of 5% methanol/dichloromethane to provide the title compound (0.10 g) having the following physical data.

Workup

  1. temperatureto warm
  2. customThe reaction was quenched with ethyl acetate/sodium hydrogen carbonate aqueous solution
  3. washthe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe solution was concentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-2977449e520e49af9ba59fbf43e8fc51
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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