Toluene → HCID 66680851, compound

HRID 1626753Notes

Reaction equation

HRID 1626753 reaction equation
C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:15]1[CH:16]=[C:17]([C:21]([NH:23][C:24]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:25]=2[C:26]([O:28][CH3:29])=[O:27])=[O:22])[CH:18]=[CH:19][CH:20]=1.[CH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38](B(O)O)=[CH:37][N: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.C(OCC)(=O)C.O.CO>[Cl:34][C:31]1[CH:32]=[CH:33][C:24]([NH:23][C:21]([C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:38]3[C:39]4[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH:35]=[N:36][CH:37]=3)[CH:16]=2)=[O:22])=[C:25]([CH:30]=1)[C:26]([O:28][CH3:29])=[O:27]

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 3761204Isoquinoline-4-boronic acidHCID 60794708HCID 60794708, compound

Product 1

HCID 66680851HCID 66680851, compoundYield 63.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Under an Ar atmosphere, 10 mL of toluene, 2.5 mL of methanol, and 2.5 mL of 2M aqueous sodium carbonate solution were added to 500 mg (1.36 mmol) of methyl 2-{[(3-bromophenyl)carbonyl]amino}-5-chlorobenzoate obtained in Example 8-(i) and 352 mg (2.03 mmol) of isoquinolin-4-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 7 hours. The mixture was cooled to room temperature, and then water and ethyl acetate were added, followed by collection by filtration, water-washing, and drying. Thereafter, the resultant was dissolved in chloroform and filtered. The filtrate was condensed, thereby giving 360 mg of methyl 5-chloro-2-({[3-(isoquinolin-4-yl)phenyl]carbonyl}amino)benzoate (yield: 63%).

Workup

  1. customthe mixture was degassed
  2. temperaturethe mixture was heated
  3. temperatureThe 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. filtrationfiltered
  9. customcondensed

Sources & evidence

ORD record
ord-0f7ef2399bf342d9895a870a7bb502da
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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