Potassium Carbonate → 5-(4-chloro-2-(pyridin-4-yl)phenyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide

HRID 1473294Notes

Reaction equation

HRID 1473294 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([S:19]([NH:22][C:23]1[S:27][N:26]=[CH:25][N:24]=1)(=[O:21])=[O:20])=[CH:14]2.C(=O)([O-])[O-].[K+].[K+].[N:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1.O1CCOCC1>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.O>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH:11]=[CH:12][C:13]([S:19]([NH:22][C:23]2[S:27][N:26]=[CH:25][N:24]=2)(=[O:21])=[O:20])=[CH:14]3)=[C:2]([C:37]2[CH:38]=[CH:39][N:34]=[CH:35][CH:36]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 2734379(Pyridin-4-yl)boronic acidHCID 866873495-(2-Bromo-4-chlorophenyl)-N-(1,2,4-thiadiazol-5-YL)naphthalene-2-sulfonamide

Product 1

HCID 866873525-(4-chloro-2-(pyridin-4-yl)phenyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamideYield 6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A pressure vessel was charged with 5-(2-bromo-4-chlorophenyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (80 mg, 0.166 mmol), potassium carbonate (115 mg, 0.832 mmol), pyridin-4-ylboronic acid (30.7 mg, 0.250 mmol), tetrakis(triphenylphosphine)palladium(0) (19.23 mg, 0.017 mmol), dioxane (1109 μl) and water (555 μl). The reaction mixture was heated in a microwave at 100° C. for 30 min. The mixture was then cooled to room temperature and the organic layer was separated from the aqueous layer by pipet. The resulting organic layer was then injected as is onto a reverse phase HPLC for purification (Column: Xbridge 19×100 mm, 5 μm, Waters, Milford, Mass., Flow rate: 40 mL/min, Mobile phase: 0.1% TFA in ACN and water). The fractions containing product were dried under a vacuum to provide 5-(4-chloro-2-(pyridin-4-yl)phenyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (5 mg, 0.01 mmol) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.54 (s, 2H) 7.04 (d, J=5.98 Hz, 2H) 7.36-7.41 (m, 1H) 7.46 (d, J=8.76 Hz, 1H) 7.51-7.60 (m, 2H) 7.63-7.70 (m, 3H) 8.09 (d, J=8.33 Hz, 1H) 8.16 (s, 1H) 8.26 (d, J=5.56 Hz, 2H) 8.39 (d, J=1.71 Hz, 1H); m/z (ESI) 479.0 (M+H)+.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customthe organic layer was separated from the aqueous layer by pipet
  3. customas is onto a reverse phase HPLC for purification (Column: Xbridge 19×100 mm, 5 μm, Waters, Milford, Mass., Flow rate: 40 mL/min, Mobile phase: 0.1% TFA in ACN and water)
  4. additionThe fractions containing product
  5. customwere dried under a vacuum

Sources & evidence

ORD record
ord-8b0f2cab59ef4e35bc65371d2b1d2c0b
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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