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

HRID 712592노트

반응식

HRID 712592 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a8a54079a8954de2806a76c5369a52d4
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181272B2

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