Sodium Carbonate → HCID 131735917, compound

HRID 2207423Notes

Reaction equation

HRID 2207423 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[CH3:10][C:11]1[CH:12]=[C:13]([NH:26][C:27]2[N:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][N:28]=2)[CH:14]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[CH3:10][C:11]1[CH:16]=[C:15]([C:2]2[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=2)[CH:14]=[C:13]([NH:26][C:27]2[N:32]=[C:31]([C:33]([F:36])([F:34])[F:35])[CH:30]=[CH:29][N:28]=2)[CH:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 98775625-Bromopyridine-2-carbaldehydeHCID 58456089N-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine

Product 1

HCID 131735917HCID 131735917, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-bromopyridine-2-carbaldehyde (500 mg, 2.69 mmol), N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (1.23 g, 3.24 mmol), PdCl2(dppf) (216 mg, 0.295 mmol), sodium carbonate (2 M, 2.70 mL, 5.40 mmol), and dioxane (10.0 mL) was evacuated and purged with Ar(g) (3×), and then irradiated under microwave at 100° C. for 10 minutes. The mixture was filtered, diluted with ethyl acetate and washed with water. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography (25% ethyl acetate in hexanes) to afford 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carbaldehyde. C18H14F3N4O [M+H]+ 359. found 359.

Workup

  1. customwas evacuated
  2. custompurged with Ar(g) (3×)
  3. customirradiated under microwave at 100° C. for 10 minutes
  4. filtrationThe mixture was filtered
  5. additiondiluted with ethyl acetate
  6. washwashed with water
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customthe residue was purified by silica gel chromatography (25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f6deffd9d1c7485fbd1d097558eef0c4
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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