Sodium Carbonate → HCID 68762948, compound

HRID 1878623Notes

Reaction equation

HRID 1878623 reaction equation
I[C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[Br:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[N:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.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>[Br:12][C:13]1[CH:14]=[C:15]([C:2]2[CH:3]=[CH:4][C:5]([CH2:8][N:9]([CH3:11])[CH3:10])=[CH:6][N:7]=2)[CH:16]=[N:17][CH:18]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 38148115-Bromopyridine-3-boronic acid2×HCID 86632432HCID 86632432, compound2×

Product 1

HCID 68762948HCID 68762948, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 20074477Dimethoxyethane ethanolSolvent

Procedure

To a solution of (6-iodo-pyridin-3-ylmethyl)-dimethyl-amine (Intermediate 219) (1 eq, 3.89 mmol, 1.02 g) in DME/EtOH (1:1, 10 ml) are added 5-bromo-pyridine-3-boronic acid (Intermediate 100) (1.1 eq, 4.28 mmol, 0.864 g), Pd(PPh3)4 (0.05 eq, 0.195 mmol, 0.225 g), and aqueous Na2CO3 solution (4M, 3 eq, 11.7 mmol, 2.92 ml). The resulting mixture is heated using microwave radiation at 130° C. for 20 min. The mixture is filtered through a pad of Celite and concentrated under reduced pressure. 2M aqueous HCl is added, and the mixture is washed with DCM. The aqueous layer is adjusted to pH 11 using aqueous NaOH, and extracted with DCM. The organic layer is dried over MgSO4, and the solvents are removed in vacuo. The crude mixture is purified using reversed phase HPLC to give the title compound; [M+H]+=292/294.

Workup

  1. temperatureThe resulting mixture is heated
  2. customat 130° C.
  3. customfor 20 min
  4. filtrationThe mixture is filtered through a pad of Celite
  5. concentrationconcentrated under reduced pressure
  6. addition2M aqueous HCl is added
  7. washthe mixture is washed with DCM
  8. extractionextracted with DCM
  9. dry with materialThe organic layer is dried over MgSO4
  10. customthe solvents are removed in vacuo
  11. customThe crude mixture is purified

Sources & evidence

ORD record
ord-6c0d27bde4544810a1df6681bfaba3b2
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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