Trimethyltin chloride → HCID 59305031, 화합물

HRID 2240250노트

반응식

HRID 2240250 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:9]=[C:10](I)[C:3]=12.C([Li])(C)(C)C.[CH3:27][Sn:28](Cl)([CH3:30])[CH3:29].[F-].[K+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:9]=[C:10]([Sn:28]([CH3:30])([CH3:29])[CH3:27])[C:3]=12

참가 물질

6

반응물 4

HCID 14016Trimethyltin chlorideHCID 522689Potassium FluorideHCID 53438252N-Tosyl-4-chloro-3-iodo-7-azaindoleHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 59305031HCID 59305031, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

In a Schlenk flask (dried by heating under high vacuum and venting with argon), 1.0 g of 4-chloro-3-iodo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine (2.31 mmol) is initially charged in anhydrous THF (30 ml) and cooled to −78° C. 2.85 ml of tert-butyllithium (1.7 M in pentane) (4.85 mmol) is then slowly added dropwise, and the mixture is stirred at −78° C. for 30 min. 2.42 ml of a 1 M solution of trimethyltin chloride in THF are then added dropwise, and the mixture is allowed to warm to RT overnight. 10 ml of a saturated potassium fluoride solution are then added, and the organic phase is separated off and extracted once with ethyl acetate. The combined organic phases are dried over magnesium sulfate, and the solution is concentrated. The product is purified by column chromatography on silica gel (mobile phase: toluene/ethyl acetate 20:1).

후처리

  1. temperatureto warm to RT overnight
  2. customthe organic phase is separated off
  3. extractionextracted once with ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. concentrationthe solution is concentrated
  6. customThe product is purified by column chromatography on silica gel (mobile phase: toluene/ethyl acetate 20:1)

출처 및 근거

ORD 기록
ord-dce448d63f2b4082b095192af23a8491
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723347B2

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