Sodium Carbonate → 6-Methoxy-3-phenyl-pyridin-2-yl-amine

HRID 2120758Notes

Reaction equation

HRID 2120758 reaction equation
Br[C:2]1[C:3]([NH2:10])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH3:9][O:8][C:5]1[N:4]=[C:3]([NH2:10])[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 234358793-Bromo-6-methoxypyridin-2-amine

Product 1

HCID 234358856-Methoxy-3-phenyl-pyridin-2-yl-amineYield 71%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 330 mg (1.625 mmol) 3-bromo-6-methoxy-pyridin-2-yl-amine, 396 mg (3.25 mmol) phenylboronic acid, 1 ml 2N Na2CO3 and 59 mg (0.08 mmol) dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium (II) dichloromethane adduct in 10 ml dioxane was heated to 110° C. for 2 h. The mixture was concentrated, diluted Na2CO3 aq. was added and extracted 2× with 100 ml diethyl ether. The combined organic phases were dried with MgSO4 and evaporated. The residue was purified by flash column chromatography on silica-eluting with a gradient of hexane/ethyl acetate to yield 230 mg (71%) of the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted Na2CO3 aq. was added
  3. extractionextracted 2× with 100 ml diethyl ether
  4. dry with materialThe combined organic phases were dried with MgSO4
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica-
  7. washeluting with a gradient of hexane/ethyl acetate

Sources & evidence

ORD record
ord-9459bf1eb975400ab64ae5207aa1d350
Source dataset
uspto-grants-2004_02
Patent number
US06693116B2

Reaction notes

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