Sodium Carbonate → HCID 86656162, compound

HRID 1192470Notes

Reaction equation

HRID 1192470 reaction equation
[N:1]([CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1Br)[CH3:5])=[N+:2]=[N-:3].[F:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[N:22][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C(OCC)(=O)C.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>[N:1]([CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[C:20]1[CH:21]=[N:22][CH:23]=[C:18]([F:17])[CH:19]=1)[CH3:5])=[N+:2]=[N-:3]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 86656158HCID 86656158, compound

Product 1

HCID 86656162HCID 86656162, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2(1-azidoethyl)-1-bromonaphthalene (0.080 g, 0.29 mmol) and (5-fluoropyridin-3-yl)boronic acid (49.0 mg, 0.348 mmol) in 1,4-dioxane (2 mL) was added a 1 M solution of sodium carbonate in water (0.34 mL) and tetrakis(triphenylphosphine)palladium(0) (16.7 mg, 0.0145 mmol). The reaction mixture was heated at 100° C. overnight. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with water and brine, dried over MgSO4, and then concentrated. The residue was purified on silica gel, eluting with 0 to 50% EtOAc in hexane, to give the desired product. LCMS calculated for C17H14FN4(M+H)+: m/z=293.1; found: 293.0.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel
  6. washeluting with 0 to 50% EtOAc in hexane

Sources & evidence

ORD record
ord-04c73dcddb764a92987fb3bac50b0564
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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