Toluene → HCID 66680475, compound

HRID 1626751Notes

Reaction equation

HRID 1626751 reaction equation
C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:14][O:15][C:16](=[O:34])[C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[NH:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29](I)[CH:28]=1)=[O:26].[N:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[C:37](B(O)O)[CH:36]=1>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.O.CO>[Cl:23][C:21]1[CH:20]=[CH:19][C:18]([NH:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:37]3[CH:36]=[N:35][C:44]4[C:39]([CH:38]=3)=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:28]=2)=[O:26])=[C:17]([CH:22]=1)[C:16]([O:15][CH3:14])=[O:34]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2734663Quinoline-3-boronic acidHCID 63524758HCID 63524758, compound

Product 1

HCID 66680475HCID 66680475, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Under an Ar atmosphere, 9 mL of toluene, 2.5 mL of methanol, 2.5 mL of 2M aqueous sodium carbonate solution were added to 500 mg (1.20 mmol) of 5-chloro-2-{[(3-iodophenyl)carbonyl]amino}benzoic acid methyl ester and 330 mg (1.91 mmol) of quinolin-3-ylboronic acid, and the mixture was degassed. Further, 100 mg (0.087 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was heated under stirring at 90° C. for 6 hours. After the mixture was cooled to room temperature, water was added thereto, followed by collection by filtration, water-washing, and drying. Thereafter, the resultant was dissolved in chloroform, followed by filtration. The filtrate was condensed, thereby giving 340 mg of methyl 5-chloro-2-({[3-(quinolin-3-yl)phenyl]carbonyl}amino)benzoate (yield: 67%).

Workup

  1. customthe mixture was degassed
  2. temperaturethe mixture was heated
  3. temperatureAfter the mixture was cooled to room temperature
  4. filtrationfollowed by collection by filtration, water-
  5. washwashing
  6. customdrying
  7. dissolutionThereafter, the resultant was dissolved in chloroform
  8. filtrationfollowed by filtration
  9. customcondensed

Sources & evidence

ORD record
ord-484a4724225b4093962e74b9904e163f
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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