Hydrogen Bromide → HCID 20250690, compound

HRID 1284902Notes

Reaction equation

HRID 1284902 reaction equation
[N:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH:4]=[N:3][C:2]=1N.[BrH:15].N([O-])=O.[Na+]>[Cu]Br>[Br:15][C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[N:1]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 13321939HCID 13321939, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20250690HCID 20250690, compound

Reagents, catalysts & solvents 1

HCID 24593copper(I) bromideCatalyst

Conditions

Temperature
0 °C

Procedure

A solution is prepared from 2 g of 2-amino-5H-pyrimido[5,4-b]indole (Example 7) in 25 ml of 48% strength hydrobromic acid and combined at 0° C. with 6 ml of a 2N sodium nitrite solution. The mixture is stirred into a solution of 2.1 g of copper(I) bromide in 20 ml of 24% strength hydrobromic acid. The mixture is then stirred for 20 minutes at 0° C., then briefly heated on a steam bath. The cooled-off reaction mixture is extracted with a mixture of 9 parts of ethyl acetate and one part of ethanol. The residue is evaporated and chromatographed on silica gel with a mixture of 20 parts of methylene chloride and one part of methanol, thus obtaining 0.2 g of 2-bromo-5H-pyrimido[5,4-b]indole.

Workup

  1. temperaturebriefly heated on a steam bath
  2. customThe cooled-off reaction mixture
  3. extractionis extracted with a mixture of 9 parts of ethyl acetate and one part of ethanol
  4. customThe residue is evaporated
  5. customchromatographed on silica gel with a mixture of 20 parts of methylene chloride and one part of methanol

Sources & evidence

ORD record
ord-e9f7ba151d244e45b8deeac4526784c2
Source dataset
uspto-grants-1986_01
Patent number
US04564610

Reaction notes

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