Sodium Carbonate → HCID 67070084, compound

HRID 2390828Notes

Reaction equation

HRID 2390828 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:5]=[C:6]([Br:8])[CH:7]=1.[CH3:13][O:14][C:15]1[C:20](B(O)O)=[CH:19][CH:18]=[CH:17][N:16]=1.C([O-])([O-])=O.[Na+].[Na+]>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.CO.C(Cl)Cl>[Br:8][C:6]1[CH:7]=[C:2]([C:20]2[C:15]([O:14][CH3:13])=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:3]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27611701,3-dibromo-5-tert-butylbenzeneHCID 2762709(2-Methoxypyridin-3-yl)boronic acid

Product 1

HCID 67070084HCID 67070084, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

step 1—A sealed tube containing 3,5-dibromo-tert-butylbenzene (1.00 g, 3.425 mmol, CASRN 129316-09-2), 37 (522 mg, 3.413 mmol), Pd(PPh3)4 (194 mg, 0.168 mmol) and Na2CO3 (942 mg, 8.888 mmol) and a mixture of MeOH/DCM (8/2 10 mL) was irradiated in a microwave synthesizer at 100° C. for 10 min. The organic volatiles were removed under reduced pressure. The residue was partitioned between EtOAc and water. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with a EtOAc/hexane gradient (0 to 2% EtOAc) to afford 0.633 g (58%) of 3-(3-bromo-5-tert-butyl-phenyl)-2-methoxy-pyridine (122) as a colorless oil.

Workup

  1. customstep 1—A sealed tube
  2. customwas irradiated in a microwave synthesizer at 100° C. for 10 min
  3. customThe organic volatiles were removed under reduced pressure
  4. customThe residue was partitioned between EtOAc and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified by SiO2 chromatography
  10. washeluting with a EtOAc/hexane gradient (0 to 2% EtOAc)

Sources & evidence

ORD record
ord-125c74f39ca144e7826d36dcd7a20298
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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