Cesium carbonate → 1H-Pyrrolo[2,3-B]pyridine, 5-methyl-1-[(4-methylphenyl)sulfonyl]-

HRID 1853495ノート

反応式

HRID 1853495 の反応式
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.[B-](F)(F)(F)[CH3:22].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.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]>[CH3:22][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 224773531H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(4-methylphenyl)sulfonyl]-HCID 23692566Potassium Trifluoro(methyl)borate

生成物 1

HCID 497589241H-Pyrrolo[2,3-B]pyridine, 5-methyl-1-[(4-methylphenyl)sulfonyl]-収率 47%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 5-bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (5 g, 14.29 mmol), potassium trifluoro(methyl)borate (2.62 g, 21.43 mmol), cesium carbonate (12.56 g, 38.57 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.16 g, 1.43 mmol) in THF (150 mL) and water (15 mL) was heated at reflux for 18 hours. The reaction mixture was cooled down to ambient and partitioned between EtOAc (100 mL) and water (100 mL). The organic phase was separated, washed with 1N HCl (100 mL) and brine (100 mL), then, dried over magnesium sulfate and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to give the title compound as a white solid (1.903 g, 47% yield).

後処理

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction mixture was cooled down to ambient and
  3. custompartitioned between EtOAc (100 mL) and water (100 mL)
  4. customThe organic phase was separated
  5. washwashed with 1N HCl (100 mL) and brine (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on silica gel by flash column chromatography

出典と根拠

ORDレコード
ord-c78f03ee54904d779d5bb013b34af7a4
出典データセット
uspto-grants-2015_02
特許番号
US08962642B2

反応ノート

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