Sodium Bicarbonate → HCID 90414955, compound

HRID 2271463Notes

Reaction equation

HRID 2271463 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([O:17][CH3:18])=[N:10][C:11]([CH3:16])=[C:12]([CH:15]=2)[C:13]#N)[CH:5]=[CH:6][CH:7]=1.BrC1C(OC)=NC(C)=C(C=1)C#N.[Cl:31]C1C=C(B(O)O)C=CC=1.C(=O)(O)[O-].[Na+]>C(#N)C>[Cl:31][CH2:13][C:12]1[C:11]([CH3:16])=[N:10][C:9]([O:17][CH3:18])=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH:15]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 90414872HCID 90414872, compoundHCID 90414959HCID 90414959, compound

Product 1

HCID 90414955HCID 90414955, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

5-(3-Chlorophenyl)-6-methoxy-2-methylnicotinonitrile. A 20 mL microwave vial was charged with 5-bromo-6-methoxy-2-methylnicotinonitrile (1.2 g, 5.28 mmol), (3-chlorophenyl)boronic acid (990 mg, 6.3 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride DCM complex (191 mg, 0.26 mmol), ACN (10 mL) and saturated aq. sodium bicarbonate (3 mL). The vial was sealed, purged with nitrogen and heated at 100° C. under microwave irradiation for 10 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 as an off white solid (995 mg, 74%). [M+H]=259.06.

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-f346a9fbc9cd4a4689b44a930795e3ba
Source dataset
uspto-grants-2015_09
Patent number
US09120770B2

Reaction notes

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