Sodium Carbonate → HCID 68781447, compound

HRID 2264440Notes

Reaction equation

HRID 2264440 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[CH:19][C:18](Br)=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B(O)(O)[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[CH:19][C:18]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 68781024HCID 68781024, compound

Product 1

HCID 68781447HCID 68781447, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a degassed solution of 4-(5-bromo-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (0.87 g, 2.44 mmol, 1.0 equiv) in dimethoxyethane (10 mL) was added pyridyl-3-boronic acid (0.60 g, 4.87 mmol, 2.0 equiv; commercially available), tetrakis(triphenylphosphine) palladium(0) (84.6 mg, 0.07 mmol, 0.03 equiv) and an aqueous solution of 2 M sodium carbonate (5.6 mL) and the reaction mixture heated by microwave irradiation under Ar to 130° C. for 30 min. The crude reaction mixture was extracted with ethyl acetate (3×50 mL) and the combined organic phases washed with a sat. solution of sodium chloride (2×50 mL). The organic phase was dried over MgSO4, concentrated by evaporation under reduced pressure and the residue purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of dichloromethane/methanol providing 0.68 g (76%) of the title compound. MS (ISP): 356.3 [M+H]+.

Workup

  1. customThe crude reaction mixture
  2. extractionwas extracted with ethyl acetate (3×50 mL)
  3. washthe combined organic phases washed with a sat. solution of sodium chloride (2×50 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customthe residue purified by silica column chromatography
  7. washeluting with a gradient of dichloromethane/methanol providing 0.68 g (76%) of the title compound

Sources & evidence

ORD record
ord-f690d2e5afce48bb9c3d93f8332de14a
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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