Methanol → HCID 136082432, compound

HRID 1198517Notes

Reaction equation

HRID 1198517 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[C:14](=[O:28])[N:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:16]4[N:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:12]=3[NH:11][N:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[C:14](=[O:28])[N:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:16]4[N:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:12]=3[NH:11][N:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 19102720HCID 19102720, compound

Product 1

HCID 136082432HCID 136082432, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In an argon atmosphere, 2.3 g (6.2 millimoles) of Compound 11 obtained in Example 11 was dissolved in 100 ml of methylene chloride. The solution was cooled to 0° C. Slowly 1.8 ml (18.7 millimoles) of boron tribromide was added to the solution, and the mixture was stirred at room temperature for 7 hours. The reaction mixture was cooled to 0° C., and then 30 ml of methanol was added. The mixture was stirred at room temperature for 30 minutes. 3/4 volume of the solvent was evaporated under reduced pressure. 18 ml of 3N hydrochloric acid was added. The precipitate was collected by filtration, and recrystallized from DMF-water to obtain 2.1 g (yield: 96.3%) of Compound 14.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. custom3/4 volume of the solvent was evaporated under reduced pressure
  4. addition18 ml of 3N hydrochloric acid was added
  5. filtrationThe precipitate was collected by filtration
  6. customrecrystallized from DMF-water

Sources & evidence

ORD record
ord-07c59f0c97a3479bb342d2e5f88850ab
Source dataset
uspto-grants-1994_01
Patent number
US05281610

Reaction notes

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