1,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl ester → HCID 57496002, compound

HRID 2071140Notes

Reaction equation

HRID 2071140 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C([Sn](CCCC)(CCCC)[C:21]1[CH:26]=[N:25][CH:24]=[CH:23][N:22]=1)CCC>C1(C)C=CC=CC=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>[N:22]1[CH:23]=[CH:24][N:25]=[CH:26][C:21]=1[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterHCID 27373162-(Tributylstannyl)pyrazine

Product 1

HCID 57496002HCID 57496002, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To dimethyl 5-bromoisophthalate (617 mg, 2.26 mmol) in toluene (10 ml), 2-tributylstannyl pyrazine (1 g, 2.71 mmol) was added followed by Pd(PPh3)4 (102 mg, 0.09 mmol). Then reaction mixture was refluxed for 22 h. Then the reaction mixture was filtered through celite and volatiles were removed under vacuum. Crude residue was column chromatographed (50% ethylacetate/50% Hexanes) to obtain 455 mg of dimethyl 5-(pyrazin-2-yl)isophthalate as a pale yellow solid.

Workup

  1. customThen reaction mixture
  2. temperaturewas refluxed for 22 h
  3. filtrationThen the reaction mixture was filtered through celite and volatiles
  4. customwere removed under vacuum
  5. customchromatographed (50% ethylacetate/50% Hexanes)

Sources & evidence

ORD record
ord-610a8378f60e40f98c22046adcda26a7
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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