1,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl ester → HCID 58188082, compound

HRID 1845290Notes

Reaction equation

HRID 1845290 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].[CH3:16][C:17]1[CH:18]=[CH:19][C:20]([Sn](CCCC)(CCCC)CCCC)=[N:21][CH:22]=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.C1(C)C=CC=CC=1>[CH3:16][C:17]1[CH:18]=[CH:19][C:20]([C:2]2[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=2)[C:7]([O:9][CH3:10])=[O:8])=[N:21][CH:22]=1

Participants

5

Reactant 2

HCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterHCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridine

Product 1

HCID 58188082HCID 58188082, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of dimethyl 5-bromoisophthalate (1.0 g, 3.66 mmol), 5-methyl-2-(tributylstannyl)pyridine (1.5 mL, 4.5 mmol), tetrakis(triphenylphosphine)palladium(0) (200 mg, 0.17 mmol), and toluene (10 mL) under nitrogen was subjected to microwave irradiation at 120° C. for 2 hour. The mixture was cooled to room temperature and the precipitate was collected via filtration and rinsed with hexane to afford a white solid which was the desired product. The filtrate was purified via flash chromatography to afford another crop of the desired product (0.8 g in total). LC-MS: 286.3 [M+1]+; 1H NMR (400 MHz, CDCl3): 8.84 (d, J=1.6 Hz, 2H), 8.71 (t, J=1.6 Hz, 1H), 8.56 (t, J=0.8 Hz, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.61 (dd, J=2.0, 8.1 Hz, 1H), 3.98 (s, 6H), 2.41 (s, 3H).

Workup

  1. customirradiation at 120° C. for 2 hour
  2. filtrationthe precipitate was collected via filtration
  3. washrinsed with hexane
  4. customto afford a white solid which

Sources & evidence

ORD record
ord-7b848cb7091d44fe90d866d988478c3d
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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