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

HRID 269491Notes

Reaction equation

HRID 269491 reaction equation
CS([N:5]1[C:9]2=[N:10][CH:11]=[C:12](B3OC(C)(C)C(C)(C)O3)[CH:13]=[C:8]2[CH:7]=[CH:6]1)(=O)=O.Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=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:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:12]1[CH:13]=[C:8]2[CH:7]=[CH:6][NH:5][C:9]2=[N:10][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 497590461-(Methanesulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 598322245-(2-Pyridinyl)-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 1-methanesulfonyl-5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (300 mg, 0.93 mmol) and 2-bromopyridine (150 mg, 0.95 mmol) in DMF (3 mL) was added aqueous Na2CO3 (2M, 1.9 mL, 3.8 mmol). To this suspension was then added PdCl2(dppf) (60 mg, 0.075 mmol) under N2 atmosphere. The flask was then covered with septa, heated at 80° C. for 9 h, and poured into water (30 mL). The aqueous solution was extracted with ethylacetate (3×30 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated. The resulting residue was dissolved in MeOH (10 mL) and treated with 6N NaOH solution (2 mL) at 50° C. for 3 h. After evaporating the MeOH, the aqueous residue was acidified with 6N HCl to pH=8. The precipitate was collected by filtration, washed with water, and dried on the pump for direct use (100 mg off-white solid, 0.51 mmol). MS (ES+): m/e=196.1 (M+H); LC: 2.04 min.

Workup

  1. extractionThe aqueous solution was extracted with ethylacetate (3×30 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe resulting residue was dissolved in MeOH (10 mL)
  6. additiontreated with 6N NaOH solution (2 mL) at 50° C. for 3 h
  7. customAfter evaporating the MeOH
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with water
  10. dry with materialdried on the pump for direct use (100 mg off-white solid, 0.51 mmol)
  11. custom2.04 min.

Sources & evidence

ORD record
ord-77da14bcc6b5489b986090249bb98baf
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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