N-bromobutanimide → HCID 178461196, compound

HRID 1852704Notes

Reaction equation

HRID 1852704 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:15]2[N:16]([CH2:19][C@H:20]3[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]3)[CH:17]=[N:18][C:14]=2[CH:13]=[C:12]([Cl:27])[N:11]=1>C(Cl)(Cl)Cl.ClCCl>[Br:1][C:17]1[N:16]([CH2:19][C@H:20]2[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]2)[C:15]2[C:10]([Cl:9])=[N:11][C:12]([Cl:27])=[CH:13][C:14]=2[N:18]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 178461251HCID 178461251, compound

Product 1

HCID 178461196HCID 178461196, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

N-bromosuccinimide (3.28 g, 18.4 mmol) was added to a solution of 4,6-dichloro-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (Preparative Example 2.3, 5 g, 16.8 mmol) stirring in degassed chloroform (168 mL) at room temperature. The reaction was heated to reflux for 1 hour. The mixture was cooled to room temperature, diluted with dichloromethane, and washed with saturated aqueous sodium thiosulfate (2×) and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient) to afford 2-bromo-4,6-dichloro-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine. MS ESI calc'd. for C14H16BrCl2N3 [M+H]+ 378. found 378.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 hour
  3. washwashed with saturated aqueous sodium thiosulfate (2×) and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record
ord-634118a9a5c444e18e2dcdd302bcf3e1
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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