Toluene → HCID 22031561, compound

HRID 1792519Notes

Reaction equation

HRID 1792519 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12](B(O)O)=[CH:11][N:10]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:9]=2)=[CH:4][CH:3]=1.Br[C:36]1[CH:37]=[CH:38][C:39]2[N:40]([C:42]([C:45]3[S:46][C:47]([S:50][CH3:51])=[CH:48][CH:49]=3)=[CH:43][N:44]=2)[CH:41]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:36]3[CH:37]=[CH:38][C:39]4[N:40]([C:42]([C:45]5[S:46][C:47]([S:50][CH3:51])=[CH:48][CH:49]=5)=[CH:43][N:44]=4)[CH:41]=3)=[CH:11][N:10]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 22031633HCID 22031633, compoundHCID 22032084HCID 22032084, compound

Product 1

HCID 22031561HCID 22031561, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

736 mg 3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolylboronic acid (compound in Production Example 25), 550 mg 6-bromo-3-[5-(methylsulfanyl)-2-thienyl]imidazo[1,2-a]-pyridine (compound in Production Example 58) and 100 mg tetrakis (triphenylphosphine)palladium were stirred at 80° C. for 3 hours in a solution mixture of 5 mL toluene, 5 mL ethanol and 2.5 mL of 2 N aqueous sodium carbonate under nitrogen atmosphere. The reaction solution was extracted with ethyl acetate, the organic layer was dried over magnesium sulfate, the solvent was removed, and the resulting residue was purified by NH silica gel column chromatography (hexane/ethyl acetate) to give 685 mg of the title compound (pale greenish yellow crystals; recrystallization solvent, ethyl acetate/methanol).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. customthe solvent was removed
  4. customthe resulting residue was purified by NH silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e0a40e1389a5425c8e20f1e27a7c1270
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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