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

HRID 383299Notes

Reaction equation

HRID 383299 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.[N:12]1([C:17]2[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=2)[CH:16]=[CH:15][CH:14]=[N:13]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:21]3[CH:20]=[CH:19][CH:18]=[C:17]([N:12]4[CH:16]=[CH:15][CH:14]=[N:13]4)[CH:22]=3)=[CH:3][N:4]=[C:5]2[CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 16640530(3-(1H-pyrazol-1-yl)phenyl)boronic acidHCID 467391183-Bromo-7-chloroimidazo[1,2-a]pyridine

Product 1

HCID 252629807-Chloro-3-(3-pyrazol-1-yl-phenyl)-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, 2.59 mmol, 600 mg) and 3-(1H-pyrazolyl)-phenylboronic acid (1.2 eq, 1.04 mmol, 195 mg) are dissolved in DME (5 ml) and water (1.5 ml) and Na2CO3 (0.65 eq, 1.68 mmol, 209 mg) is added. PdCl2(PPh3)2 (0.04 eq, 0.104 mmol, 72.8 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 9:1 DCM/MeOH to yield 7-chloro-3-(3-pyrazol-1-yl -phenyl)-imidazo[1,2-a]pyridine as a brown solid; [M+H]+=295

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 9:1 DCM/MeOH

Sources & evidence

ORD record
ord-24142fe5affc419f924fdbdd05330ef1
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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