Toluene → HCID 10224467, compound

HRID 2293470Notes

Reaction equation

HRID 2293470 reaction equation
Br[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[N:3]=1.[C:27]1(C)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1(OB(O)O)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>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.C(O)C>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:4]2[N:3]=[C:2]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:7]([C:8]#[N:9])=[CH:6][C:5]=2[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 10296372HCID 10296372, compound

Product 1

HCID 10224467HCID 10224467, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 0.1 g (0.23 mMol) of 2-bromo-6-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-pyridine-3-carbonitrile (Example 3), 10 ml of toluene and 4 ml of ethanol was added 34 mg (0.28 mMol) of phenylboric acid and a solution of 71 mg (0.52 mMol) of K2CO3 in 1 ml water. To the resulting reaction mixture was added 18 mg of tetrakis(triphenylphosphine)palladium. The mixture was held at reflux overnight, cooled to room temperature, poured into 75 ml of water and extracted with dichloromethane. The combined organic solutions were washed once with 10% NaOH solution, once with brine, dried over MgSO4 and evaporated to dryness to give a yellowish oil which crystallized upon standing. Trituration with ether gave 74.5 mg (76%) of a white powder: m.p. 230°-231° C.

Workup

  1. customTo the resulting reaction mixture
  2. temperatureat reflux overnight
  3. extractionextracted with dichloromethane
  4. washThe combined organic solutions were washed once with 10% NaOH solution, once with brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customto give a yellowish oil which
  8. customcrystallized

Sources & evidence

ORD record
ord-64601842edb645ccb8d5856eb541fadf
Source dataset
uspto-grants-1997_11
Patent number
US05686470

Reaction notes

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