Water → 5-(Pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 269490Notes

Reaction equation

HRID 269490 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8](S(C)(=O)=O)[C:5]2=[N:6][CH:7]=1.[N:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[C:4]3[CH:10]=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 497588975-Bromo-1-(methanesulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 533199325-(Pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-1-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine (140 mg, 0.51 mmol) and 4-pyridinyl boronic acid (125 mg, 1.02 mmol) in DMF (4 mL) was added aqueous Na2CO3 (2M, 1.3 mL, 2.6 mmol). To this suspension was then added PdCl2(dppf) (20 mg, 0.025 mmol) under N2 atmosphere. The flask was then covered with septa, heated at 80° C. for 9 h, and poured into water. The precipitate was collected by filtration, washed with water, and redissolved in MeOH (10 mL). To this Methanol solution was added 6N NaOH solution (2 mL) and the resulting basic reaction mixture was heated at 50° C. for 3 h. After evaporating the MeOH, the aqueous residue was acidified with 6N HCl to pH=2. The precipitate was filtered off and washed with 2N HCl. The acidic filtrate was then neutralized with saturated NaHCO3 solution. The crude product was collected by filtration, washed with water, and dried on the pump for direct use (60 mg, 0.31 mmol). LC/MS: Rt 1.96 mins.; m/e 196.1 (M+H).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. dissolutionredissolved in MeOH (10 mL)
  4. additionTo this Methanol solution was added 6N NaOH solution (2 mL)
  5. temperaturethe resulting basic reaction mixture was heated at 50° C. for 3 h
  6. customAfter evaporating the MeOH
  7. filtrationThe precipitate was filtered off
  8. washwashed with 2N HCl
  9. filtrationThe crude product was collected by filtration
  10. washwashed with water
  11. customdried on the pump for direct use (60 mg, 0.31 mmol)

Sources & evidence

ORD record
ord-b661ba4b4576428eafe887accdb75d8b
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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