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

반응식

HRID 79553 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-af45adbbb64e4ec3845891795d75ed55
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841304B2

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