Sodium Carbonate → 5-phenyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

HRID 2300281Notes

Reaction equation

HRID 2300281 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>C1(C)C=CC=CC=1.C(O)C.C(Cl)(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C>[C:12]1([C:2]2[CH:3]=[C:4]3[C:8](=[N:9][CH:10]=2)[NH:7][C:6](=[O:11])[CH2:5]3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

10

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 433294Lithium ChlorideHCID 155040625-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one

Product 1

HCID 155040635-phenyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-oneYield 51.4%

Reagents, catalysts & solvents 5

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred mixture of 5-bromo-7-azaoxindole (213 mg, 1 mmol) and phenylboronic acid (183 mg, 1.5 mmol) in toluene (6 ml) and ethanol (6 ml) were added 1 M sodium carbonate solution (2.5 ml, 2.5 mmol), lithium chloride (127 mg, 3 mmol) and dichlorobis(triphenylphosphine)palladium(II) (35 mg, 0.05 mmol) under N2 atmosphere. The reaction mixture was heated to reflux at 95° C. for 18 hours. The reaction mixture was diluted with chloroform (50 ml) and washed with brine (20 ml). The aqueous layer was thoroughly extracted with chloroform. The combined organic layers were dried over anhydrous MgSO4, filtered and evaporated under vacuum to give crude product. Trituation of the crude product with diethyl ether yielded 5-phenyl-7-azaoxindole as a yellow solid (108 mg, 51.4%). 1H NMR (DMSO-d6): δ 11.04 (s, 1H), 8.32 (s, 1H), 7.83 (s, 1H), 7.60 (d, 2H, J=7.4 Hz), 7.44 (t, 2H, J=7.4 Hz), 7.32 (t, 1H, J=7.4 Hz), 3.58 (s, 2H). MS (−ve APCI): 210 (48, M+), 209 (100, M−H).

Workup

  1. temperatureThe reaction mixture was heated
  2. washwashed with brine (20 ml)
  3. extractionThe aqueous layer was thoroughly extracted with chloroform
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customto give crude product

Sources & evidence

ORD record
ord-d841e62aa3c841319343d212f3e2c6fd
Source dataset
uspto-grants-2002_12
Patent number
US06498176B1

Reaction notes

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