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Ethylene Glycol → HCID 86754308, compound

HRID 583364
Notes
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Reaction equation

HRID 583364 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

HCID 86754308HCID 86754308, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-487aa5ca48534794830f67d7c48fa2c7
Source dataset
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05929097

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes