Sodium Carbonate → HCID 22177239, compound

HRID 1797171Notes

Reaction equation

HRID 1797171 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH:5]([C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1)[C:6]#[N:7].C1(C)C=CC=CC=1.CCO.C([O-])([O-])=O.[Na+].[Na+].B1([C:41]2[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=2)OC(C)(C)C(C)(C)O1>CCOC(C)=O.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.CO.C(Cl)Cl>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH:5]([C:8]1[CH:13]=[CH:12][C:11]([C:41]2[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=2)=[CH:10][CH:9]=1)[C:6]#[N:7]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 21863594Toluene ethanolHCID 22177243HCID 22177243, compound

Product 1

HCID 22177239HCID 22177239, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-dimethylamino-2-(4-iodo-phenyl)-butyronitrile (1.02 g, 3.2 mmol) in 2:1 toluene/EtOH (30 mL) was added 2M Na2CO3 (10 mL, 20 mmol), pyridine-4-boronic acid pinacol cyclic ester (1.0 g, 4.9 mmol), and Pd(PPh3)4 (116 mg, 0.31 mmol). The resulting mixture was heated at 90° C. under Ar for 16 h. TLC (10% MeOH/CH2Cl2) showed no starting material left. The mixture was diluted with EtOAc (100 mL), washed with saturated aqueous NaHCO3 (50 mL×3), saturated aqueous NaCl (50 mL×3), dried over Na2SO4 and concentrated by rotary evaporation. The crude residue was purified using silica gel chromatography (2–10% MeOH/CH2Cl2 gradient) to give 4-dimethylamino-2-(4-pyridin-4-yl-phenyl)-butyronitrile as a brown oil, 680 mg (80%). 1H NMR (300 MHz, CDCl3): δ 8.79 (dd, 2H), 7.78 (d, 2H), 7.60 (m, 4H), 4.22 (dd, 1H), 2.61 (m, 1H), 2.46 (m, 1H), 2.37 (s, 6H), 2.24 (m, 1H), 2.15 (m, 1H).

Workup

  1. waitleft
  2. washwashed with saturated aqueous NaHCO3 (50 mL×3), saturated aqueous NaCl (50 mL×3)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe crude residue was purified

Sources & evidence

ORD record
ord-72142db74f064115816c378e9e99205f
Source dataset
uspto-grants-2006_04
Patent number
US07034056B2

Reaction notes

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