1,2-Dimethoxyethane → HCID 54354029, compound

HRID 1266316Notes

Reaction equation

HRID 1266316 reaction equation
COCCOC.[CH2:7]([O:9][C:10]([C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:21]=1[N:22]([S:30]([C:33]1[CH:38]=[CH:37][C:36](Br)=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[CH:19][CH:18]=[C:17]([C:40]([F:43])([F:42])[F:41])[CH:16]=2)=[O:11])[CH3:8].[C:44]1(B(O)O)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.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>[CH2:7]([O:9][C:10]([C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:21]=1[N:22]([S:30]([C:33]1[CH:38]=[CH:37][C:36]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[CH:19][CH:18]=[C:17]([C:40]([F:43])([F:42])[F:41])[CH:16]=2)=[O:11])[CH3:8]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 54458871HCID 54458871, compound

Product 1

HCID 54354029HCID 54354029, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 8.5 mL of degassed ethylene glycol dimethyl ether, was added 500 mg (0.85 mmol) of the ester, 110 mg (0.93 mmol) of phenylboronic acid, 80 mg (0.07 mmol) of tetrakis(triphenylphosphine)palladium and 1.1 ml (2.2 mmol) of 2M aqueous Na2CO3 and the mixture ws heated to reflux under nitrogen for 36 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 to give 4-[(biphenyl-4-sulfonyl)-pyridin-3-ylmethyl-amino]-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester.

Workup

  1. temperaturethe mixture ws heated
  2. temperatureto reflux under nitrogen for 36 hr
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a56784c8e0543e79990a397d303124b
Source dataset
uspto-grants-2003_04
Patent number
US06548524B2

Reaction notes

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