3-bromo-4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine → 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-3-methyl-5-phenyl-1-(phenylsulfonyl)-

HRID 79553

反応式

HRID 79553 の反応式
[Cl-].[CH3:2][Zn+].Br[C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]=2[Cl:14])[N:7]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH:6]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:14][C:12]1[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][N:9]=[C:8]2[N:7]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[CH:6]=[C:5]([CH3:2])[C:13]=12

参加物

5

反応物 2

HCID 687614313-bromo-4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 178477797HCID 178477797、化合物

生成物 1

HCID 687612621H-Pyrrolo[2,3-b]pyridine, 4-chloro-3-methyl-5-phenyl-1-(phenylsulfonyl)-収率 87.8%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

Methyl zinc chloride (3.35 mL, 6.70 mmol) was added to 3-bromo-4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.00 g, 2.23 mmol) and Pd(PPh3)4 (0.129 g, 0.111 mmol) in THF (10 mL). The reaction was then heated to 80° C. for 2 hours, cooled to room temperature, and quenched with saturated NH4Cl. The resulting solids were filtered and discarded. The filtrate was diluted with DCM (500 mL) and was washed with water. The combined organic fractions were dried, filtered, and concentrated to give a crude solid that was purified by column chromatography (2:1 DCM:hexanes) to give 4-chloro-3-methyl-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.75 g, 87.7% yield).

後処理

  1. temperaturecooled to room temperature
  2. customquenched with saturated NH4Cl
  3. filtrationThe resulting solids were filtered
  4. additionThe filtrate was diluted with DCM (500 mL)
  5. washwas washed with water
  6. customThe combined organic fractions were dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a crude solid that
  10. customwas purified by column chromatography (2:1 DCM:hexanes)

出典と根拠

ORDレコード
ord-af45adbbb64e4ec3845891795d75ed55
出典データセット
uspto-grants-2014_09
特許番号
US08841304B2

関連ノート

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