Ethanol → 3-(3-Pyrazol-1-yl-phenyl)-7-pyridin-3-yl-imidazo[1,2-a]pyridine

HRID 383268Notes

Reaction equation

HRID 383268 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N:17]4[CH:21]=[CH:20][CH:19]=[N:18]4)[CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1.CCO.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[N:17]1([C:13]2[CH:12]=[C:11]([C:8]3[N:5]4[CH:6]=[CH:7][C:2]([C:24]5[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=5)=[CH:3][C:4]4=[N:10][CH:9]=3)[CH:16]=[CH:15][CH:14]=2)[CH:21]=[CH:20][CH:19]=[N:18]1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 252629807-Chloro-3-(3-pyrazol-1-yl-phenyl)-imidazo[1,2-a]pyridine

Product 1

HCID 252296803-(3-Pyrazol-1-yl-phenyl)-7-pyridin-3-yl-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

7-Chloro-3-(3-pyrazol-1-yl-phenyl)-imidazo[1,2-a]pyridine (Intermediate AA) (1 eq, 0.214 mmol, 70 mg) and 3-pyridine boronic acid (1 eq, 0.214 mmol, 26.1 mg) are dissolved in DME (3 ml), EtOH (1 ml) and water (1.5 ml) and Na2CO3 (2 eq, 0.427 mmol, 53.0 mg) is added. Pd(PPh3)4 (0.06 eq, 0.01 mmol, 15 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 8:2 DCM/MeOH to yield 3-(3-pyrazol-1-yl-phenyl)-7-pyridin-3-yl-imidazo[1,2-a]pyridine as a light brown solid; [M+H]+=338

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 8:2 DCM/MeOH

Sources & evidence

ORD record
ord-cdc9094ecc2e4109a6b7b52b18818a07
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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