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Ethyl 4-(bromomethyl)picolinate → HCID 59508608, 화합물

HRID 1095930
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HRID 1095930 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([OH:23])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:22])[C:9]([OH:21])([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=1)[C:10]([F:13])([F:12])[F:11].[CH2:24]([O:26][C:27]([C:29]1[CH:34]=[C:33]([CH2:35]Br)[CH:32]=[CH:31][N:30]=1)=[O:28])[CH3:25]>CN(C=O)C.C(=O)([O-])[O-].[Ag+2]>[CH2:24]([O:26][C:27]([C:29]1[CH:34]=[C:33]([CH2:35][O:23][C:4]2[CH:5]=[CH:6][C:7]([CH:8]([CH3:22])[C:9]([OH:21])([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=3)[C:10]([F:13])([F:11])[F:12])=[C:2]([Cl:1])[CH:3]=2)[CH:32]=[CH:31][N:30]=1)=[O:28])[CH3:25]
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참가 물질

5

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HCID 21781508Ethyl 4-(bromomethyl)picolinateHCID 252541463-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenol

생성물 1

HCID 59508608HCID 59508608, 화합물수율 63%

시약·촉매·용매 2

HCID 178418647HCID 178418647, 화합물촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenol (100 mg, obtained in Example 93, step 6) and ethyl-4-(bromomethyl)-pyridine-2-carboxylate (85 mg, [CAS Reg. No. 153994-03-7]) were dissolved in DMF (5 mL) followed by addition of silver carbonate (80 mg). The mixture was heated to 80° C. for 3 hours. The reaction mixture was cooled, poured into ice/water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a yellow foam (98 mg, 63%). MS (m/e)=509.3 [MH+].

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted two times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

출처 및 근거

ORD 기록
ord-54837cd5ac4f459284d38e8ceecb1617
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08138189B2

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