Water → HCID 86656161, compound

HRID 1192468Notes

Reaction equation

HRID 1192468 reaction equation
[N:1]([CH:4]([C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([CH3:14])=[N:11][C:10]=2[C:15]=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:7]=[CH:8][C:9]2[S:13][C:12]([CH3:14])=[N:11][C:10]=2[C:15]=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 86656160HCID 86656160, compound

Product 1

HCID 86656161HCID 86656161, compoundYield 83.8%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

To a mixture of 5-(1-azidoethyl)-4-bromo-2-methyl-1,3-benzothiazole (0.100 g, 0.336 mmol) and (3-fluorophenyl)boronic acid (56.5 mg, 0.404 mmol) in 1,4-dioxane (2 mL) was added a 1 M solution of sodium carbonate in water (0.40 mL, 22 mmol) and tetrakis(triphenylphosphine)palladium(0) (19.4 mg, 0.0168 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 crude mixture was purified on silica gel, eluting with 0 to 40% EtOAc in hexane, to give the desired product (88 mg, 83%). LCMS calculated for C16H14FN4S(M+H)+: m/z=313.1; found: 313.0.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude mixture was purified on silica gel
  6. washeluting with 0 to 40% EtOAc in hexane

Sources & evidence

ORD record
ord-9e9681ba77fa44e7bdd392087ad3e038
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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