Hydrogen Bromide → HCID 57503314, compound

HRID 916667Notes

Reaction equation

HRID 916667 reaction equation
[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]4[N:20]=[C:21](N)[N:22]=[C:16]4[C:15]=3[CH2:24][CH2:25][CH3:26])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.N([O-])=O.[Na+].[NH4+].[OH-].[BrH:33]>O>[Br:33][C:21]1[N:22]=[C:16]2[N:17]([CH:18]=[N:19][C:14]([CH2:13][N:9]3[CH:10]=[CH:11][N:12]=[C:8]3[C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=3)=[C:15]2[CH2:24][CH2:25][CH3:26])[N:20]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 14923Ammonium HydroxideHCID 11337106HCID 11337106, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 57503314HCID 57503314, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 174 (788 mg, 2.24 mmol) in aqueous HBr (48%, 8 ml) cooled to 0° C. is added dropwise a solution of NaNO2 (232 mg, 3.36 mmol) in water (2 ml). The mixture is stirred at 0° C. for 30 minutes and CuBr (482 mg, 3.36 mmol) is added in 3 portions. The mixture is stirred at 0° C. for 30 minutes then allowed to warm to room temperature in 2 hours. Concentrated NH4OH is added dropwise to the solution until the pH≧7. The mixture is then extracted with EtOAc (3×15 ml) and the combined extracts are washed with brine (15 ml), dried (Na2SO4) and evaporated. The brown solid obtained it washed with ether (4 ml) then hexane (6 ml), which gives 175 as a light brown solid.

Workup

  1. stirringThe mixture is stirred at 0° C. for 30 minutes
  2. temperatureto warm to room temperature in 2 hours
  3. extractionThe mixture is then extracted with EtOAc (3×15 ml)
  4. washthe combined extracts are washed with brine (15 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe brown solid obtained it
  8. washwashed with ether (4 ml)

Sources & evidence

ORD record
ord-74c15002d0304545a96d675c2c09cb71
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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