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Potassium Carbonate → ethyl 6-chloro-7-(3,5-dimethylpiperidin-1-yl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854875
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HRID 854875 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[O:8][CH:7]([C:13]([F:16])([F:15])[F:14])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5]2.[CH3:22][CH:23]1[CH2:28][CH:27]([CH3:29])[CH2:26][NH:25][CH2:24]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:25]1[CH2:26][CH:27]([CH3:29])[CH2:28][CH:23]([CH3:22])[CH2:24]1)[O:8][CH:7]([C:13]([F:16])([F:15])[F:14])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5]2
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5

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HCID 11430Potassium CarbonateHCID 1182593,5-DimethylpiperidineHCID 21883602ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

생성물 1

HCID 69516147ethyl 6-chloro-7-(3,5-dimethylpiperidin-1-yl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate수율 93.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

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온도
90 °C

실험 절차

A mixture of ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate (from Example 7a, Step 2) (0.5 g, 1.54 mmole) and 3,5-dimethylpiperidine (0.17 g, 1.54 mmole) was dissolved in anhydrous DMF (5 mL), warmed to 90° C. and treated with K2CO3 (0.25 g, 1.84 mmole). The solution was maintained at 90° C. for 48 hrs, cooled to room temperature, filtered through celite and condensed to a viscous oil. The oil was purified by Biotage silica chromatography with 30% methylene chloride in hexane to give light yellow oil (0.6 g, 93%). GCMS m/z 417.00 (M+). 1H NMR (CDCl3/300 MHz) 7.61 (s, 1H), 7.18 (s, 1H), 6.60 (s, 1H), 5.67 (q, 1H, J=7.0 Hz), 4.67 (m, 2H), 3.40 (m, 2H), 2.18 (m, 2H), 1.86 (m, 2H), 1.31 (m, 3H), 1.04 (m, 1H), 0.90 (m, 6H), 0.68 (m, 1H).

후처리

  1. temperatureThe solution was maintained at 90° C. for 48 hrs
  2. temperaturecooled to room temperature
  3. filtrationfiltered through celite and condensed to a viscous oil
  4. customThe oil was purified by Biotage silica chromatography with 30% methylene chloride in hexane

출처 및 근거

ORD 기록
ord-9a76a3c845b1420d87f132b4ed0547ee
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07259266B2

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