Acetone → HCID 18923469, compound

HRID 1899990Notes

Reaction equation

HRID 1899990 reaction equation
Cl.Cl.[NH2:3][C:4]1[C:5]([Cl:24])=[C:6]([C:20]([Cl:23])=[CH:21][CH:22]=1)[CH2:7][O:8][C:9]1[C:10]2[N:11]([C:15]([Br:19])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1.[CH3:25][C:26]([CH3:28])=O.C([BH3-])#N.[Na+]>Cl.C(O)C>[Br:19][C:15]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][C:6]3[C:20]([Cl:23])=[CH:21][CH:22]=[C:4]([NH:3][CH:26]([CH3:28])[CH3:25])[C:5]=3[Cl:24])[C:10]2=[N:17][C:16]=1[CH3:18]

Participants

6

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 189233178-(3-Amino-2,6-dichlorobenzyloxy)-3-bromo-2-methylimidazo[1,2-a]pyridine dihydrochloride

Product 1

HCID 18923469HCID 18923469, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a mixture of 8-(3-amino-2,6-dichlorobenzyloxy)-3-bromo-2-methylimidazo[1,2-a]pyridine dihydrochloride (100 mg) and acetone (116 mg) in 3M HCl solution in ethanol (2 ml) was added sodium cyanoborohydride (25 mg) in one portion. The mixture was stirred for 2 hours at ambient temperature and then concentrated in vacuo. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was dried and concentrated in vacuo to give an oil, which was purified by preparative thin-layer chromatography on silica gel (ethyl acetate:n-hexane =1:2, V/V), to give 3-bromo-8-(2,6-dichloro-3-isopropylaminobenzyloxy)-2-methylimidazo[1,2-a]pyridine as a white solid (50 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo
  5. customto give an oil, which
  6. customwas purified by preparative thin-layer chromatography on silica gel (ethyl acetate:n-hexane =1:2, V/V)

Sources & evidence

ORD record
ord-6b3b7a8761124d9ea7fa77ec323b30d4
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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