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Ethylene Glycol → HCID 86754308, 화합물

HRID 583364
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HRID 583364 반응식
C(O)CO.[CH3:5][O:6][C:7](=[O:35])[C:8]1[CH:13]=[C:12](Br)[CH:11]=[C:10]([CH3:15])[C:9]=1[N:16]([S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1.[CH:36]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1B(O)O)=[O:37].C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.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>[CH3:5][O:6][C:7]([C:8]1[CH:13]=[C:12]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[CH:36]=[O:37])[CH:11]=[C:10]([CH3:15])[C:9]=1[N:16]([S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:35]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 700538645-Bromo-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-3-methyl-benzoic acid methyl ester

생성물 1

HCID 86754308HCID 86754308, 화합물수율 94%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8857Ethyl Acetate용매

실험 절차

To 5 ml of degassed ethylene glycol dirncthyl ether, was added 505.4 mg (1.0 mmol) of the product of Example 89, 165 mg (1.1 mmol) of 2-formylbenzene boronic acid, 58 mg (0.05 mmol) of tetrakis(triphenylphosphine)palladium and 1 ml (2.0 mmol) of 2M aqueous Na2CO3 and the mixture ws heated to reflux under nitrogen for 18 hr. The reaction was cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel with EtOAc/Hexane (1:1) as eluant to provide 499 mg (94%) of the desired product as an yellow solid. Electrospray Mass Spec 531 (M+H).

후처리

  1. temperaturethe mixture ws heated
  2. temperatureto reflux under nitrogen for 18 hr
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel with EtOAc/Hexane (1:1) as eluant

출처 및 근거

ORD 기록
ord-487aa5ca48534794830f67d7c48fa2c7
출처 데이터셋
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05929097

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