Stannous chloride dihydrate → 4-(1-(2-methoxyethyl)-1H-pyrrolo[3,2-b]pyridin-7-ylthio)benzenamine

HRID 1013733노트

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HRID 1013733 반응식
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[S:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH:7]=[CH:6]1.O.O.[Sn](Cl)Cl>CO>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[S:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH:7]=[CH:6]1

참가 물질

4

반응물 2

HCID 61436Stannous chloride dihydrateHCID 673166791-(2-methoxyethyl)-7-(4-nitrophenylthio)-1H-pyrrolo[3,2-b]pyridine

생성물 1

HCID 594273624-(1-(2-methoxyethyl)-1H-pyrrolo[3,2-b]pyridin-7-ylthio)benzenamine

시약·촉매·용매 1

HCID 887Methanol용매

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온도
50 °C

실험 절차

A sealed vial was charged with 1-(2-methoxyethyl)-7-(4-nitrophenylthio)-1H-pyrrolo[3,2-b]pyridine (0.147 g, 0.446 mmol) and methanol (5 mL). Tin (II) chloride dihydrate (0.504 g, 2.23 mmol) was added and the reaction was stirred at 50° C. for 3 hours. The reaction was concentrated and dissolved in DCM. The solution was washed with saturated sodium bicarbonate solution, which was extracted with DCM. The combined organic layers were washed with water, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (gradient elution 0-10% DCM:MeOH) to afford 4-(1-(2-methoxyethyl)-1H-pyrrolo[3,2-b]pyridin-7-ylthio)benzenamine as an orange oil that solidified under high vacuum. MS: M+H+=300.1.

후처리

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in DCM
  3. washThe solution was washed with saturated sodium bicarbonate solution, which
  4. extractionwas extracted with DCM
  5. washThe combined organic layers were washed with water
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe material was purified via column chromatography (gradient elution 0-10% DCM:MeOH)

출처 및 근거

ORD 기록
ord-6761ee55712045b3bf85baac766711a5
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981891B2

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