Bromine → HCID 58910714, compound

HRID 1643249Notes

Reaction equation

HRID 1643249 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[N:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=2)[CH:6]=1.[Br:16]Br>Br.CC(O)=O>[Br:16][CH2:14][C:13]([C:10]1[CH:11]=[N:12][C:7]([N:5]2[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]2)=[CH:8][CH:9]=1)=[O:15]

Participants

4

Reactant 2

HCID 24408BromineHCID 450967261-(6-(4-Methyl-1H-imidazol-1-yl)pyridin-3-yl)ethanone

Product 1

HCID 58910714HCID 58910714, compoundYield 124.9%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

Compound 19 (6.1 g, 30.30 mmol) was suspended in 30% HBr/AcOH (75 ml). Bromine (4.82 g, 30.30 mmol) was added dropwise over 1 h. The reaction was stirred for 2 h at room temperature. The reaction mixture was poured into 600 mL of ice water and stirred rapidly for 15 min. The resulting precipitate was collected on a filter and washed with water. The compound was air dried to yield 20 as a yellow solid (10.6 g, 80%). LC/MS: [M+1]+=281.1. C11H10BrN3O:2HBr=442.0. 1H NMR (DMSO-d6) 300 MHz δ2.36 and 2.37 (6H, two s), 5.06 (2H, s), 8.16 (1H, d, J=9.0 Hz), 8.29 (1H, s), 8.69 (1H, d, J=9.0 Hz), 9.15 (1H, s), 9.93 (1H, s).

Workup

  1. stirringstirred rapidly for 15 min
  2. customThe resulting precipitate was collected on
  3. filtrationa filter
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-af1064249f3d4b39827b1fa2425fb41e
Source dataset
uspto-grants-2012_02
Patent number
US08119680B2

Reaction notes

Loading…