3-bromo-4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine → 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-3-methyl-5-phenyl-1-(phenylsulfonyl)-

HRID 79553

Reaction equation

HRID 79553 reaction equation
[Cl-].[CH3:2][Zn+].Br[C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]=2[Cl:14])[N:7]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH:6]=1>C1COCC1.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>[Cl:14][C:12]1[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][N:9]=[C:8]2[N:7]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[CH:6]=[C:5]([CH3:2])[C:13]=12

Participants

5

Reactant 2

HCID 687614313-bromo-4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 178477797HCID 178477797, compound

Product 1

HCID 687612621H-Pyrrolo[2,3-b]pyridine, 4-chloro-3-methyl-5-phenyl-1-(phenylsulfonyl)-Yield 87.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Methyl zinc chloride (3.35 mL, 6.70 mmol) was added to 3-bromo-4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.00 g, 2.23 mmol) and Pd(PPh3)4 (0.129 g, 0.111 mmol) in THF (10 mL). The reaction was then heated to 80° C. for 2 hours, cooled to room temperature, and quenched with saturated NH4Cl. The resulting solids were filtered and discarded. The filtrate was diluted with DCM (500 mL) and was washed with water. The combined organic fractions were dried, filtered, and concentrated to give a crude solid that was purified by column chromatography (2:1 DCM:hexanes) to give 4-chloro-3-methyl-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.75 g, 87.7% yield).

Workup

  1. temperaturecooled to room temperature
  2. customquenched with saturated NH4Cl
  3. filtrationThe resulting solids were filtered
  4. additionThe filtrate was diluted with DCM (500 mL)
  5. washwas washed with water
  6. customThe combined organic fractions were dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a crude solid that
  10. customwas purified by column chromatography (2:1 DCM:hexanes)

Sources & evidence

ORD record
ord-af45adbbb64e4ec3845891795d75ed55
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Linked notes

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