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

HRID 383300
Notes
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Reaction equation

HRID 383300 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](B(O)O)[CH:16]=[CH:15][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]=[CH:15][N:14]=[C:13]([Cl:12])[CH:18]=3)=[CH:3][N:4]=[C:5]2[CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 51515952-Chloropyridine-4-boronic acidHCID 467391183-Bromo-7-chloroimidazo[1,2-a]pyridine

Product 1

HCID 866443437-Chloro-3-(2-chloro-pyridin-4-yl)-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 2

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Bromo-7-chloro-imidazo-[1,2-a]-pyridine (1 eq, 6.48 mmol, 1.5 g) and 2-chloro-pyridine-4-boronic acid (1 eq, 6.48 mmol, 1.02 g) are dissolved in DME (6 ml) and water (2 ml) and Na2CO3 (2 eq, 13.0 mmol, 1.61 g) is added. PdCl2(PPh3)2 (0.06 eq, 0.389 mmol, 273 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-chloro-pyridin-4-yl)-imidazo[1,2-a]pyridine as an orange solid; [M+H]+=265

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-f80e09f6ab894d97a79d1a10967103ae
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367662B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes