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Sodium Carbonate → 6-(2,4-Dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile

HRID 420492
Notes
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Reaction equation

HRID 420492 reaction equation
Br[C:2]1[C:3]([C:11]#[N:12])=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.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>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[C:2]1[C:3]([C:11]#[N:12])=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 666589436-Bromoimidazo[1,2-a]pyridine-7-carbonitrile

Product 1

HCID 666590596-(2,4-Dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrileYield 39%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-bromo-imidazo[1,2-a]pyridine-7-carbonitrile (1.5 g, 6.8 mmol), 2,4-dichloro-benzeneboronic acid (1.9 g, 10.1 mmol), Pd(PPh3)4 (390 mg, 0.34 mmol) and Na2CO3 (2.0 M solution in water, 12 mL) in OME (30 mL) was refluxed for 14 h under an inert atmosphere of argon. The reaction mixture was cooled to RT, diluted in AcOEt (200 mL) and washed with water (200 mL). The organic layer was dried over Na2SO4, filtered, and evaporated. The residue was purified by Combi-Flash Companion™ (isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→1:1) to yield the title compound (750 mg, 2.6 mmol, 39%) as an orange foam. MS. 289 [M+1]+; HPLC: AtRet=1.50; TLC: RF 0.16 ([hexane/DCM 1:1]/TBME 3:7).

Workup

  1. temperaturewas refluxed for 14 h under an inert atmosphere of argon
  2. washwashed with water (200 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by Combi-Flash Companion™ (isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→1:1)

Sources & evidence

ORD record
ord-6fc1fea25f1e43929ec67b30c72a6e25
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08097617B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes