Sodium Carbonate → HCID 67372768, compound

HRID 1517541Notes

Reaction equation

HRID 1517541 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[CH2:14][S:15][CH3:16].[CH3:17][O:18][C:19]1[C:24](B(O)O)=[CH:23][CH:22]=[CH:21][N:20]=1.C([O-])([O-])=O.[Na+].[Na+]>CO.C(Cl)Cl.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:8]([C:6]1[C:5]([O:12][CH3:13])=[CH:4][C:3]([CH2:14][S:15][CH3:16])=[C:2]([C:24]2[C:19]([O:18][CH3:17])=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 68590523HCID 68590523, compound

Product 1

HCID 67372768HCID 67372768, compoundYield 54.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

step 2—A sealed tube containing 80 (50 mg), 2-methoxy-3-pyridine boronic acid (38 mg), Na2CO3 (43 g) and Pd(PPh3)4 (19 mg) in a mixture of MeOH (4 mL) and DCM (1 mL) was irradiated in a microwave synthesizer at 120° C. for 30 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 on a preparative SiO2 TLC plate developed with 50% EtOAc/hexane to afford 30 mg of 3-(5-tert-butyl-4-methoxy-2-methylsulfanylmethyl-phenyl)-2-methoxy-pyridine (82).

Workup

  1. customstep 2—A sealed tube
  2. customwas irradiated in a microwave synthesizer at 120° C. for 30 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 on a preparative SiO2 TLC plate

Sources & evidence

ORD record
ord-81cd2348a56641b2b5da63a560044122
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

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