Sodium Carbonate → HCID 86638339, compound

HRID 2390803Notes

Reaction equation

HRID 2390803 reaction equation
Br[C:2]1[C:3]([OH:14])=[C:4]([CH:7]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:9]=1)[CH:5]=[O:6].[CH3:15][O:16][C:17]1[C:22](B(O)O)=[CH:21][CH:20]=[CH:19][N:18]=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:10]([C:8]1[CH:9]=[C:2]([C:22]2[C:17]([O:16][CH3:15])=[N:18][CH:19]=[CH:20][CH:21]=2)[C:3]([OH:14])=[C:4]([CH:7]=1)[CH:5]=[O:6])([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 71720963-Bromo-5-tert-butyl-2-hydroxybenzaldehyde

Product 1

HCID 86638339HCID 86638339, compoundYield 77.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

step 1—A sealed tube containing 3-bromo-5-tert-butyl-2-hydroxy benzaldehyde E-1b (R1═OH, R4=tert-Bu, 858 mg, 3.339 mmol), 37 (766 mg, 5.008 mmol), Pd(PPh3)4 (240 mg, 0.208 mmol), and Na2CO3 (891 mg, 8.406 mmol) in a mixture of MeOH (10 mL) and DCM (2 mL) was irradiated in a microwave reactor at 115° C. for 30 min. The organic volatiles were removed under reduced pressure and 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 an EtOAc/hexane gradient (3 to 5% EtOAc) to afford 737 mg (77%) of 5-tert-butyl-2-hydroxy-3-(2-methoxy-pyridin-3-yl)-benzaldehyde (48) as a pale yellow oil.

Workup

  1. customstep 1—A sealed tube
  2. customwas irradiated in a microwave reactor at 115° 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 by SiO2 chromatography
  10. washeluting with an EtOAc/hexane gradient (3 to 5% EtOAc)

Sources & evidence

ORD record
ord-89f1f9d41d8045c3a94e4ff404670c0a
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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