Toluene → HCID 68762479, compound

HRID 79549Notes

Reaction equation

HRID 79549 reaction equation
Br[C:2]1[C:3]([Cl:20])=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(C)C=CC=CC=1>CCO>[Cl:20][C:3]1[C:2]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:7][N:6]=[C:5]2[N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:4]=12

Participants

5

Reactant 3

HCID 1140TolueneHCID 66827Phenylboronic AcidHCID 497588851H-Pyrrolo[2,3-B]pyridine, 5-bromo-4-chloro-1-(phenylsulfonyl)-

Product 1

HCID 68762479HCID 68762479, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyri dine (3.70 g, 9.96 mmol, see Example 6) and phenylboronic acid (1.27 g, 10.5 mmol) were placed in 2:1 toluene:EtOH (30 mL). The contents were then degassed under Ar and heated to 80° C. for 24 hours. The reaction was cooled to room temperature, diluted with DCM, and poured into water. The organic fraction was filtered, dried, and concentrated. Purification was carried out by column chromatography (1:1 to 1:2 hexane:DCM) to give 4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (3.20 g, 87.1% yield).

Workup

  1. customThe contents were then degassed under Ar
  2. temperatureThe reaction was cooled to room temperature
  3. additiondiluted with DCM
  4. additionpoured into water
  5. filtrationThe organic fraction was filtered
  6. customdried
  7. concentrationconcentrated
  8. customPurification

Sources & evidence

ORD record
ord-0dbe85217aac4e419af86599897898d1
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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