Pyridine → HCID 18923415, compound

HRID 1899995Notes

Reaction equation

HRID 1899995 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[CH:18]=[C:17]([NH:19][CH3:20])[CH:16]=[CH:15][C:14]=3[Cl:21])[C:5]2=[N:4][C:3]=1[CH3:22].N1C=CC=CC=1.[S:29](Cl)([CH3:32])(=[O:31])=[O:30]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[CH:18]=[C:17]([N:19]([CH3:20])[S:29]([CH3:32])(=[O:31])=[O:30])[CH:16]=[CH:15][C:14]=3[Cl:21])[C:5]2=[N:4][C:3]=1[CH3:22]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 18923690HCID 18923690, compound

Product 1

HCID 18923415HCID 18923415, compoundYield 34.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-8- (2-chloro-5-methylaminobenzyloxy)-2-methylimidazo[1,2-a]pyridine (60 mg), pyridine (16 mg) and 4-dimethylaminopyridine (10 mg) in methylene chloride (2 ml) was added mesyl chloride (22 mg) in one portion at 5° C., and the mixture was stirred for 9 hours at ambient temperature. The precipitate was filtered off and the residue was washed with methylene chloride and diethyl ether respectively. The filtrate was concentrated in vacuo and the residue was purified by preparative thin-layer chromatography on silica gel (methanol:methylene chloride=1:10, V/V) to give 3-bromo-8-[2-chloro-5-(N-methyl-N-methylsulfonylamino)benzyloxy]-2-methylimidazo[1,2-a]pyridine (25 mg).

Workup

  1. filtrationThe precipitate was filtered off
  2. washthe residue was washed with methylene chloride and diethyl ether respectively
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by preparative thin-layer chromatography on silica gel (methanol:methylene chloride=1:10, V/V)

Sources & evidence

ORD record
ord-98052316d16f42ccaac595e17541f646
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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