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Triethylamine → 6-Chloro-5-iodo-2-(methylsulfonyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine

HRID 715553
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HRID 715553 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[NH:11][C:10]([S:12]([CH3:15])(=[O:14])=[O:13])=[N:9][C:5]2=[N:6][C:7]=1[I:8].C(N(CC)CC)C.Cl[CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[N:11]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[N:9]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:5]2=[N:6][C:7]=1[I:8]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 895582346-Chloro-5-iodo-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine

생성물 1

HCID 1235023166-Chloro-5-iodo-2-(methylsulfonyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

6-Chloro-5-iodo-2-(methylsulfonyl)-1H-imidazo[4,5-b]pyridine (for preparation see WO 2012116145; 1.5 g) and triethylamine (875 μL) are dissolved in tetrahydrofurane (12 mL), cooled to 0° C. and treated with (2-(chloromethoxy)ethyl)trimethylsilane (SEM-Cl; 890 μL). The mixture is stirred for 30 minutes while warming to room temperature. Then the mixture is partitioned between saturated aqueous NH4Cl and ethylacetate. The organic phase is washed with water and brine. After drying (MgSO4) the solvents are evaporated in vacuo to give the title compound. LC (method 1): tR=1.22 min; Mass spectrum (ESI+): m/z=488 [M+H]+.

후처리

  1. temperaturewhile warming to room temperature
  2. customThen the mixture is partitioned between saturated aqueous NH4Cl and ethylacetate
  3. washThe organic phase is washed with water and brine
  4. dry with materialAfter drying (MgSO4) the solvents
  5. customare evaporated in vacuo

출처 및 근거

ORD 기록
ord-a7b0eeead3d24fa883a10694a7c67d27
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09187477B2

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