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Toluene → 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-(3-fluorophenyl)-1-(phenylsulfonyl)-

HRID 79525
Notes
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Reaction equation

HRID 79525 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.[F:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C([O-])([O-])=O.[K+].[K+].C1(C)C=CC=CC=1>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.CCO>[Cl:20][C:3]1[C:2]([C:26]2[CH:25]=[CH:24][CH:23]=[C:22]([F:21])[CH:27]=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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 497588851H-Pyrrolo[2,3-B]pyridine, 5-bromo-4-chloro-1-(phenylsulfonyl)-

Product 1

HCID 687616631H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-(3-fluorophenyl)-1-(phenylsulfonyl)-Yield 73.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.660 g, 1.78 mmol), 3-fluorophenylboronic acid (0.298 g, 2.13 mmol), Pd(PPh3)4 (0.103 g, 0.0888 mmol) and 10% K2CO3 (aq., 3.70 mL, 2.66 mmol) were added to an argon degassed solution of 2:1 toluene:EtOH (6 mL). The reaction was then heated to 80° C. for 18 hours. The reaction was then diluted with water and extracted with DCM. The organic fractions were dried, filtered, concentrated, and purified by column chromatography (1:1 hexanes:DCM) to give 4-chloro-5-(3-fluorophenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.508 g, 73.9% yield).

Workup

  1. extractionextracted with DCM
  2. customThe organic fractions were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography (1:1 hexanes:DCM)

Sources & evidence

ORD record
ord-9911de1f7e734dc2a130c3f4acc0a9da
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841304B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes