1,2,4-Trimethylbenzene → HCID 10296372, compound

HRID 1416962Notes

Reaction equation

HRID 1416962 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=O)[C:11]([C:15]#[N:16])=[CH:10][C:9]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.CC1C=CC(C)=CC=1C.[K+].[Br-:37]>O>[Br:37][C:12]1[C:11]([C:15]#[N:16])=[CH:10][C:9]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:13]=1

Participants

5

Reactant 3

HCID 72471,2,4-TrimethylbenzeneHCID 253877Potassium BromideHCID 15408575HCID 15408575, compound

Product 1

HCID 10296372HCID 10296372, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1,2-dihydro-6-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-2-oxo-pyridine-3-carbonitrile (Example 2, Step 3) (0.66 g, 1.81 mMol), 12 ml of 1,2,4-trimethylbenzene, 1.0 g of KBr, and 5 g of PBr5 was heated to 80° C. for 2 hours and then to 180° C. overnight. The reaction mixture was cooled to room temperature and stirred with 75 ml of water for 1 hour. The organic portion was extracted into dichloromethane. The dichloromethane extract was washed once with brine, dried over MgSO4, and evaporated to dryness. The residual oil was purified by HPLC to give 0.55 g (72% yield) of solid: m.p. 229.5-231.5° C.

Workup

  1. customto 180° C.
  2. customovernight
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionThe organic portion was extracted into dichloromethane
  5. extractionThe dichloromethane extract
  6. washwas washed once with brine
  7. dry with materialdried over MgSO4
  8. customevaporated to dryness
  9. customThe residual oil was purified by HPLC

Sources & evidence

ORD record
ord-ad70d7019b3242578e72acd82c36c3a1
Source dataset
uspto-grants-1999_06
Patent number
US05916905

Reaction notes

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