Ethyl Acetate → HCID 117667380, compound

HRID 712676Notes

Reaction equation

HRID 712676 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([C:12]([NH2:14])=[O:13])[CH2:7][CH2:6][CH2:5]2.[CH:15]([C:17]1[CH:18]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:20]=[N:21][CH:22]=1)=[O:16].C(=O)([O-])[O-].[Na+].[Na+].CCOC(C)=O>O1CCOCC1.O.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]>[CH:15]([C:17]1[CH:18]=[C:19]([C:2]2[CH:3]=[C:4]3[C:9](=[N:10][CH:11]=2)[N:8]([C:12]([NH2:14])=[O:13])[CH2:7][CH2:6][CH2:5]3)[CH:20]=[N:21][CH:22]=1)=[O:16]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 49926405-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbaldehydeHCID 117667602HCID 117667602, compound

Product 1

HCID 117667380HCID 117667380, compoundYield 60.6%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-bromo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (500 mg, 2.0 mmol) in a mixture of 1,4-dioxane (9 mL) and water (1 mL) is added 5-formylpyridine-3-boronic acid pinacol ester (501 mg, 2.1 mmol), sodium carbonate (290 mg; 2.7 mmol), and 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium (II) (159 mg, 0.20 mmol). The resultant mixture is stirred at 100° C. for 2 h. EtOAc is added and the mixture is washed with saturated aqueous sodium bicarbonate solution, brine and is dried (MgSO4). The solvent is evaporated and the crude product is purified by silica gel column (0-10% MeOH in DCM) to afford 6-(5-formyl-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (342 mg).

Workup

  1. washthe mixture is washed with saturated aqueous sodium bicarbonate solution, brine
  2. dry with materialis dried (MgSO4)
  3. customThe solvent is evaporated
  4. customthe crude product is purified by silica gel column (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-e851863f06354cf189a93ad92aaed29d
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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