Ethanol → HCID 23537392, compound

HRID 1792426Notes

Reaction equation

HRID 1792426 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:22](B(O)O)=[CH:21][N:20]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:19]=2)=[CH:14][CH:13]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[F:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:22]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([CH:8]=[CH:9][N:10]=4)[CH:7]=3)=[CH:21][N:20]([C:26]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:19]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27955476-Bromoimidazo[1,2-a]pyridineHCID 22032084HCID 22032084, compound

Product 1

HCID 23537392HCID 23537392, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.2 g 6-bromoimidazo[1,2-a]pyridine, 6 g 3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolylboronic acid (compound in Production Example 25), and 647 mg tetrakistriphenyl phosphine palladium were heated in a solution mixture of 30 mL ethanol, 30 mL toluene and 17 mL of 2 N aqueous sodium carbonate at 80° C. for 2 hours in a stream of nitrogen. The reaction solution was cooled to room temperature, ethyl acetate was added thereto, and the organic layer was dried over magnesium sulfate. After filtration, the organic solvent was evaporated, and the residue was dissolved in dichloromethane and purified by NH silica gel (hexane/ethylacetate). The resulting solid was recrystallized from ethyl acetate/hexane, to give 4.65 g of the title compound as colorless crystals.

Workup

  1. dry with materialthe organic layer was dried over magnesium sulfate
  2. filtrationAfter filtration
  3. customthe organic solvent was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. custompurified by NH silica gel (hexane/ethylacetate)
  6. customThe resulting solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-11e0cb72b6b940c093fc6fa91043590f
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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