Sodium Bicarbonate → HCID 90415047, compound

HRID 578821Notes

Reaction equation

HRID 578821 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10](N)[CH:11]=[N:12][C:13]=2[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.[Br:17]C1C=C(N)C=NC=1OC.C(=O)(O)[O-].[Na+]>C(#N)C>[Br:17][C:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:13]([O:14][CH3:15])=[N:12][CH:11]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 213107125-Bromo-6-methoxypyridin-3-amineHCID 90414658HCID 90414658, compound

Product 1

HCID 90415047HCID 90415047, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

5-(3-Chlorophenyl)-6-methoxypyridin-3-amine. A 10 mL microwave vial was charged with 5-bromo-6-methoxypyridin-3-amine (2.00 g, 10 mmol) (3-chlorophenyl)boronic acid (1.87 g, 12 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride DCM complex (365 mg, 0.45 mmol), ACN (6 mL) and saturated aq. sodium bicarbonate (3 mL). The vial was sealed, purged with nitrogen and heated at 110° C. for 15 min. The layers were separated and the aq. phase extracted with EtOAc. The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification (FCC, SiO2, 0-50%, EtOAc/hexanes) afforded the title compound (1.95 g, 84%) which was taken on directly to the next step.

Workup

  1. customThe vial was sealed
  2. custompurged with nitrogen
  3. customThe layers were separated
  4. extractionthe aq. phase extracted with EtOAc
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. customthe solvent was removed under reduced pressure
  7. customPurification (FCC, SiO2, 0-50%, EtOAc/hexanes)

Sources & evidence

ORD record
ord-a529594c5c784f498f27d41b3cf54305
Source dataset
uspto-grants-2015_05
Patent number
US09040692B2

Reaction notes

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