Water → 7-Chloro-3-(2,6-dichloro-pyridin-4-yl)-imidazo[1,2-a]pyridine

HRID 383319Notes

Reaction equation

HRID 383319 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:5]2=[N:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[C:17](B2OC(C)(C)C(C)(C)O2)[CH:16]=[C:15]([Cl:28])[N:14]=1.O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:11][C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:17]3[CH:16]=[C:15]([Cl:28])[N:14]=[C:13]([Cl:12])[CH:18]=3)=[CH:3][N:4]=[C:5]2[CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 445163862,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 467391183-Bromo-7-chloroimidazo[1,2-a]pyridine

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Bromo-7-chloro-imidazo[1,2-a]pyridine (1 eq, 3.02 mmol, 700 mg) and 2,6-dichloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (1.1 eq, 3.32 mmol, 1.01 g) are dissolved in DME (4 ml) and water (1 ml) and Na2CO3 (1.5 eq, 5.53 mmol, 562 mg) is added. PdCl2(PPh3)2 (0.1 eq, 0.3 mmol, 212 mg) is added and the reaction mixture is heated using microwave radiation at 120° C. for 15 min. At the completion of this time the solvent is removed in vacuo and the reaction mixture is purified by flash column chromatography eluting with 9:1 DCM/MeOH to yield 7-chloro-3-(2,6-dichloro-pyridin-4-yl)-imidazo[1,2-a]pyridine as a yellow solid; [M+H]+=299

Workup

  1. temperaturethe reaction mixture is heated
  2. customat 120° C.
  3. customfor 15 min
  4. customAt the completion of this time the solvent is removed in vacuo
  5. customthe reaction mixture is purified by flash column chromatography
  6. washeluting with 9:1 DCM/MeOH

Sources & evidence

ORD record
ord-6000b44755944df5bd3517ca750018c6
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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