Iodine → HCID 46913420, compound

HRID 1025388Notes

Reaction equation

HRID 1025388 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](I)=[CH:9][N:10]=2)[CH:7]=1.Br[C:13]1[CH:14]=[CH:15][C:16]2[N:17](C=CN=2)[CH:18]=1.[C:22]([O-:25])(=O)C.[Na+].II.[CH3:29][OH:30]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:13]3[CH:18]=[N:17][C:16]([O:25][CH3:22])=[C:15]([O:30][CH3:29])[CH:14]=3)=[CH:9][N:10]=2)[CH:7]=1

Participants

6

Reactant 5

HCID 807IodineHCID 887MethanolHCID 517045Sodium AcetateHCID 27955476-Bromoimidazo[1,2-a]pyridineHCID 220316326-Bromo-3-iodoimidazo(1,2-a)pyridine

Product 1

HCID 46913420HCID 46913420, compound

Conditions

Temperature
0 °C

Procedure

6-bromo-3-iodoimidazo[1,2-a]pyridine. To a 150 mL round bottomed flask was added 6-bromoimidazo[1,2-a]pyridine (5.00 g, 25.4 mmol), anhydrous sodium acetate (5.69 g, 69.4 mmol) and MeOH (60 mL). The resulting mixture was cooled to 0° C. followed by adding iodine (7.13 g, 28.1 mmol). After the addition, ice bath was removed. It was warmed up to rt and continued to stir for 20 h. The precipitate in the reaction mixture was collected by filtration. The precipitate was washed with MeOH and dried to afford the desired product as light grey solid (7.0 g). MS (ESI pos. ion) m/z: 322.8. Calcd exact mass for C7H4BrIN2: 321.9. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.30 (d, J=10.82 Hz, 1H) 7.52 (d, J=9.50 Hz, 1H) 7.71 (s, 1H) 8.29 (s, 1H).

Workup

  1. additionAfter the addition, ice bath
  2. customwas removed
  3. temperatureIt was warmed up to rt
  4. filtrationThe precipitate in the reaction mixture was collected by filtration
  5. washThe precipitate was washed with MeOH
  6. customdried

Sources & evidence

ORD record
ord-1a0b96fbb4f44861aabd4a062fe7d89b
Source dataset
uspto-grants-2014_05
Patent number
US08729074B2

Reaction notes

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