Water → HCID 86656157, compound

HRID 1192460Notes

Reaction equation

HRID 1192460 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]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.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:22]1[CH:21]=[CH:20][CH:19]=[C:18]([F:17])[CH:23]=1)[CH3:5])=[N+:2]=[N-:3]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 86656158HCID 86656158, compound

Product 1

HCID 86656157HCID 86656157, compoundYield 41.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 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 (3-fluorophenyl)boronic acid (48.6 mg, 0.348 mmol) in 1,4-dioxane (2 mL) was added a 1 M solution of sodium carbonate in water (0.34 mL, 19 mmol) and tetrakis(triphenylphosphine)palladium(0) (16.7 mg, 0.0145 mmol). The reaction mixture was heated at 100° C. overnight. After cool to room temperature, the mixture was diluted with ethyl acetate, washed with water, brine, dried over MgSO4, and then concentrated. The residue was purified on silica gel, eluting with 0 to 20% EtOAc in hexane, to give the desired product (35 mg, 41.5%). LCMS calculated for C18H14FN3Na(M+Na)+: m/z=314.1; found: 314.3.

Workup

  1. temperatureAfter cool to room temperature
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel
  6. washeluting with 0 to 20% EtOAc in hexane

Sources & evidence

ORD record
ord-2c18427f274e4d8f8384f25c8df46bd6
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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