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

HRID 712592ノート

反応式

HRID 712592 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a8a54079a8954de2806a76c5369a52d4
出典データセット
uspto-grants-2015_11
特許番号
US09181272B2

反応ノート

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