Water → HCID 22672646, compound

HRID 1369569Notes

Reaction equation

HRID 1369569 reaction equation
C[O:2][C:3]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[N:9]([C:13]([CH3:17])=[C:14]([CH3:16])[N:15]=2)[CH:10]=[CH:11][CH:12]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[N:9]([C:13]([CH3:17])=[C:14]([CH3:16])[N:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 22672579HCID 22672579, compound

Product 1

HCID 22672646HCID 22672646, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-73 °C

Procedure

8-(2-methoxy-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine (0.14 g, 0.48 mmol) was solved in methylene chloride (9 ml) and the mixture was cooled to −73° C. Boron tribromide in methylene chloride (1M) (2.37 ml, 2.37 mmol) was added dropwise and the mixture was stirred for 20 h. in a nitrogen atmosphere and the temperature was allowed to raise to room temperature. The reaction mixture was cooled on ice and ice, water and methylene chloride were added. The organic layer was separated, washed with saturated sodium bicarbonate, dried and evaporated under reduced pressure to give 0.077 g (57%) of the title compound.

Workup

  1. temperatureto raise to room temperature
  2. additionwere added
  3. customThe organic layer was separated
  4. washwashed with saturated sodium bicarbonate
  5. customdried
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-55ba9934d687466e8329360817cadf7b
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Reaction notes

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