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Sodium Iodide → Methyl 2-(2-(3-bromophenyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

HRID 1400689
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HRID 1400689 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:23]=[C:11]3[N:12]=[C:13]([CH3:22])[C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:15](Cl)[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[Na+].[I-:25]>C(#N)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:23]=[C:11]3[N:12]=[C:13]([CH3:22])[C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:15]([I:25])[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1
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참가 물질

5

반응물 2

HCID 5238Sodium IodideHCID 86710742Methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

생성물 1

HCID 86710741Methyl 2-(2-(3-bromophenyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate수율 81.3%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

Methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (1 g, 2.53 mmol) and NaI (1.519 g, 10.14 mmol) were suspended in acetonitrile (10 mL) and the resulting mixture was heated at 80° C. for 5 h. After cooling to room temp, mixture was diluted with ethyl acetate (50 mL) and washed with water (25 mL) and aqueous Na2S2O3 (25 mL), dried (Na2SO4), filtered and concentrated. Crude was then triturated with ethyl acetate/hexane to afford methyl 2-(2-(3-bromophenyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (1 g, 2.057 mmol, 81% yield) as off white solid. 1H NMR (400 MHz, CDCl3) δ: 8.20 (t, J=1.8 Hz, 1H), 7.95 (dt, J=7.8, 1.3 Hz, 1H), 7.55 (ddd, J=8.0, 2.0, 1.0 Hz, 1H), 7.36 (t, J=7.9 Hz, 1H), 7.08 (s, 1H), 4.02 (s, 2H), 3.79 (s, 3H), 2.66 (s, 3H). LCMS (M+H)=486.1.

후처리

  1. temperatureAfter cooling to room temp
  2. washwashed with water (25 mL) and aqueous Na2S2O3 (25 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customCrude was then triturated with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-0ddc1b89aaad42a2b3ff94342c6d0d0a
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08906929B2

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