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Hexane → HCID 117700526, 화합물

HRID 873527
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HRID 873527 반응식
[CH3:1][O:2][C:3]1[C:8]([CH:9]=[O:10])=[C:7]([CH3:11])[C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][CH:4]=1.[CH2:21]([O:28][C:29]1[C:30]([C:36]([O:38][CH3:39])=[O:37])=[N:31][C:32](Br)=[CH:33][CH:34]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].CCCCCC>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:21]([O:28][C:29]1[C:30]([C:36]([O:38][CH3:39])=[O:37])=[N:31][C:32]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:8]([CH:9]=[O:10])[C:7]=2[CH3:11])=[CH:33][CH:34]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 8058HexaneHCID 10340Sodium CarbonateHCID 59418684Methyl 3-(benzyloxy)-6-bromopicolinateHCID 130141572HCID 130141572, 화합물

생성물 1

HCID 117700526HCID 117700526, 화합물수율 112%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매2회
HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

A suspension of the 6-methoxy-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde produced in Example 4-1 (1.91 g, 6.92 mmol), methyl 3-(benzyloxy)-6-bromopyridine-2-carboxylate (PCT Int. Appl., 2010080478, 15 Jul. 2010) (2.23 g, 6.92 mmol), sodium carbonate (2.20 g, 20.8 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.40 g, 0.35 mmol) in 1,2-dimethoxyethane (38 ml) and water (17 ml) was prepared at room temperature, and the suspension thus prepared was then stirred at 90° C. for 3 hours. After air-cooling, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer thus obtained was dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the residue thus obtained was then purified by silica gel column chromatography (ethyl acetate:hexane=2:3, v/v) to obtain the title compound (3.02 g, yield: 112%).

후처리

  1. customwas prepared at room temperature
  2. customthe suspension thus prepared
  3. temperatureAfter air-cooling
  4. extractionthe mixed solution was then extracted with ethyl acetate
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled away under reduced pressure
  8. customthe residue thus obtained
  9. customwas then purified by silica gel column chromatography (ethyl acetate

출처 및 근거

ORD 기록
ord-f7f2795732ee4044ab17e4f7f4d00039
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08975263B2

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