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

HRID 383301Notes

Reaction equation

HRID 383301 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][N:14]=[C:13](Cl)[CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 866443437-Chloro-3-(2-chloro-pyridin-4-yl)-imidazo[1,2-a]pyridine

Product 1

HCID 684848327-Chloro-3-(2-phenyl-pyridin-4-yl)-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

7-Chloro-3-(2-chloro-pyridin-4-yl)-imidazo[1,2-a]pyridine (1 eq, 1.136 mmol, 300 mg) and phenyl boronic acid (1 eq, 1.136 mmol, 138 mg) are dissolved in DME (3 ml) and water (1 ml) and Na2CO3 (2 eq, 2.27 mmol, 282 mg) is added. PdCl2(PPh3)2 (0.1 eq, 0.114 mmol, 79.7 mg) is added and the reaction mixture is heated using microwave radiation at 120° C. for 10 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 8:2 DCM/MeOH to yield 7-chloro-3-(2-phenyl-pyridin-4-yl)-imidazo[1,2-a]pyridine as a yellow solid; [M+H]+=306

Workup

  1. temperaturethe reaction mixture is heated
  2. customat 120° C.
  3. customfor 10 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 8:2 DCM/MeOH

Sources & evidence

ORD record
ord-c667cd9b96f5413cb566301ff25e0759
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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