Dimethyl Sulfoxide → 5-Pyridin-3-yl-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carboxylic acid amide

HRID 712592Notes

Reaction equation

HRID 712592 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[CH2:15][CH2:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:2]=1.[C:16]([N:24]=C=O)(=[O:23])C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CS(C)=O>C(Cl)Cl.CCOC(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[CH2:15][CH2:14][N:13]([C:16]([NH2:24])=[O:23])[C:10]3=[N:11][CH:12]=2)[CH:2]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 675706995-pyridin-3-yl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 863055685-Pyridin-3-yl-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carboxylic acid amideYield 63.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

5-Pyridin-3-yl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (50 mg, 0.25 mmol) and benzoyl isocyanate (62 mg, 0.38 mmol) are dissolved in 1.5 mL of DCM. The mixture is heated at 50° C. for 16 hrs. Then the solvent is removed in vacuum and the residue is dissolved in 1.5 mL of EtOH. K2CO3 (60 mg, 0.43 mmol) is added and the mixture is heated at 80° C. for 55 min. The solvent is removed and the residue is partitioned between water (35 mL) and EtOAc (55 mL). The aqueous layer is separated and extracted with EtOAc (2×30 mL). The organic layers are combined and concentrated to give the crude product. To the crude product is added DMSO:EtOAc (1:3 mL) mixture and the white solid formed is filtered, rinsed with more EtOAc and dried to give 38 mg of the titled product.

Workup

  1. customThen the solvent is removed in vacuum
  2. dissolutionthe residue is dissolved in 1.5 mL of EtOH
  3. temperaturethe mixture is heated at 80° C. for 55 min
  4. customThe solvent is removed
  5. customthe residue is partitioned between water (35 mL) and EtOAc (55 mL)
  6. customThe aqueous layer is separated
  7. extractionextracted with EtOAc (2×30 mL)
  8. concentrationconcentrated
  9. customto give the crude product
  10. filtrationis filtered
  11. washrinsed with more EtOAc
  12. customdried

Sources & evidence

ORD record
ord-a8a54079a8954de2806a76c5369a52d4
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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