Potassium Carbonate → HCID 57297799, compound

HRID 24658Notes

Reaction equation

HRID 24658 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[C:4]=1B(O)O)#[N:2].C([O-])([O-])=[O:15].[K+].[K+].[CH3:20][O:21][C:22](=[O:50])[C@H:23]([CH2:35][C:36]1[CH:41]=[CH:40][C:39](OS(C(F)(F)F)(=O)=O)=[CH:38][CH:37]=1)[NH:24][C:25](=[O:34])[C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:33]>COCCOC.O.CCOC(C)=O.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>[CH3:20][O:21][C:22](=[O:50])[C@H:23]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:4]2[C:3]([C:1](=[O:15])[NH2:2])=[CH:8][CH:7]=[CH:6][C:5]=2[C:9]#[N:10])=[CH:38][CH:37]=1)[NH:24][C:25](=[O:34])[C:26]1[C:27]([Cl:33])=[CH:28][CH:29]=[CH:30][C:31]=1[Cl:32]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 22571817(2,6-Dicyanophenyl)boronic acidHCID 22970630HCID 22970630, compound

Product 1

HCID 57297799HCID 57297799, compoundYield 65.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2,6-dicyanobenzene boronic acid (0.516 g) and anhydrous K2CO3 (0.52 g) in DME/H2O (10 mL/0.5 mL) under N2 was added N-(2,6-dichlorobenzoyl)-O-(trifluoromethanesulfonyl)-L-tyrosine methyl ester (0.5 g), The catalyst Pd(PPh3)4 (0.1 g) was added and the mixture was heated at 80° C. for 5 h. The mixture was cooled, diluted with EtOAc and washed successively with water and brine. The organic layer was dried (MgSO4), evaporated, and the residue was purified by column chromatography (silica gel; eluent: EtOAc/hexane 3/1)) to yield 325 mg of N-(2,6-dichlorobenzoyl)-4-(2-cyano-6-carbamoyl-phenyl)-L-phenylalanine methyl ester. ESMS: m/z 496 (MH+), 494 (M−H)−.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed successively with water and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. customthe residue was purified by column chromatography (silica gel; eluent: EtOAc/hexane 3/1))

Sources & evidence

ORD record
ord-63da51aaf48841ae8aa3c85e908b845a
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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