Methylamine → [6-Chloro-4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-pyridin-2-yl]-methyl-amine

HRID 383320Notes

Reaction equation

HRID 383320 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[C:15]([Cl:17])[N:14]=[C:13](Cl)[CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH3:19][NH2:20].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(Cl)Cl>[Cl:17][C:15]1[N:14]=[C:13]([NH:20][CH3:19])[CH:12]=[C:11]([C:8]2[N:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]3=[N:10][CH:9]=2)[CH:16]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 10796Cesium carbonateHCID 866443467-Chloro-3-(2,6-dichloro-pyridin-4-yl)-imidazo[1,2-a]pyridine

Product 1

HCID 86644347[6-Chloro-4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-pyridin-2-yl]-methyl-amine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

7-Chloro-3-(2,6-dichloro-pyridin-4-yl)-imidazo[1,2-a]pyridine (1.0 eq, 0.64 mmol, 190 mg), methyl amine (8M in EtOH, 3.5 eq, 2.2 mmol, 0.28 ml) and Cs2CO3 (2.5 eq, 1.59 mmol, 518 mg) are dissolved in DMF (2 ml) and the reaction mixture is heated using microwave radiation at 160° C. for 30 min, it is diluted with CH2Cl2. The reaction mixture is washed with NaHCO3 and brine, dried over MgSO4, filtered and evaporated. The product is purified by flash column chromatography eluting with 8:2 DCM/MeOH to afford [6-chloro-4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-pyridin-2-yl]-methyl-amine as a brown solid; [M+H]+=294

Workup

  1. temperaturethe reaction mixture is heated
  2. customat 160° C.
  3. customfor 30 min
  4. washThe reaction mixture is washed with NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe product is purified by flash column chromatography
  9. washeluting with 8:2 DCM/MeOH

Sources & evidence

ORD record
ord-5df52912fba445f58f2c20a4f6131f7d
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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