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Trimethylsilyl iodide → 1-(3-tert-Butyl-1-p-tolyl-1H-pyrazol-5-yl)-3-((5-fluoro-2-(1-(2-oxoethyl)-1H-indazol-5-yloxy)phenyl)methyl)urea

HRID 1666758
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HRID 1666758 반응식
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[N:28]([CH2:32][CH:33](OC)[O:34]C)[N:27]=[CH:26]3)=[O:12])[N:7]([C:38]2[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].I[Si](C)(C)C>ClCCl>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[N:28]([CH2:32][CH:33]=[O:34])[N:27]=[CH:26]3)=[O:12])[N:7]([C:38]2[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 85247Trimethylsilyl iodideHCID 575522961-(3-tert-Butyl-1-p-tolyl-1H-pyrazol-5-yl)-3-((2-(1-(2,2-dimethoxyethyl)-1H-indazol-5-yloxy)-5-fluorophenyl)methyl)urea

생성물 1

HCID 575522811-(3-tert-Butyl-1-p-tolyl-1H-pyrazol-5-yl)-3-((5-fluoro-2-(1-(2-oxoethyl)-1H-indazol-5-yloxy)phenyl)methyl)urea수율 116.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

1-(3-tert-Butyl-1-p-tolyl-1H-pyrazol-5-yl)-3-((2-(1-(2,2-dimethoxyethyl)-1H-indazol-5-yloxy)-5-fluorophenyl)methyl)urea (0.500 g, 0.8324 mmol) was dissolved in dichloromethane at room temperature and iodotrimethylsilane (0.3554 mL, 2.497 mmol) added dropwise to the stirred solution. The reaction mixture was monitored by HPLC analysis and when no starting material was detected, the mixture was diluted with dichloromethane and washed with 10% aqueous Na2S2O4, saturated aqueous NaHCO3, brine, dried (MgSO4) and concentrated under reduced pressure to afford 536 mg (quant. yield) of the crude product, which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 9.76 (s, 1H), 7.97 (s, 1H), 6.78-7.30 (m, 10H), 6.17 (s, 1H), 5.99 (br, 1H), 5.44 (q, 1H, J=6.1 Hz), 4.46 (m, 4H), H 2.35 (s, 3H), 1.34 (s, 9H).

후처리

  1. washwashed with 10% aqueous Na2S2O4, saturated aqueous NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-de079668ea0f499eb04c111f9e6b1c0f
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08044083B2

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