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

HRID 1473295
Notes
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Reaction equation

HRID 1473295 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([N:15](CC1C=CC(OC)=CC=1OC)[C:16]1[S:20][N:19]=[CH:18][N:17]=1)(=[O:14])=[O:13])=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].[Cl:38][C:39]1[CH:44]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:42]=[CH:41][C:40]=1B(O)O.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:38][C:39]1[CH:44]=[C:43]([C:45]([F:46])([F:47])[F:48])[CH:42]=[CH:41][C:40]=1[C:10]1[CH:11]=[CH:2][CH:3]=[C:8]2[C:9]=1[CH:4]=[CH:5][C:6]([S:12]([NH:15][C:16]1[S:20][N:19]=[CH:18][N:17]=1)(=[O:13])=[O:14])=[CH:7]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 2783251[2-Chloro-4-(trifluoromethyl)phenyl]boronic acidHCID 866873455-bromo-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide2×

Product 1

HCID 866873535-(2-chloro-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide
Yield 10%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A pressure vessel was charged with 5-bromo-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (Intermediate D) (110 mg, 0.211 mmol), potassium carbonate (146 mg, 1.057 mmol), (2-chloro-4-(trifluoromethyl)phenyl)boronic acid (56.9 mg, 0.254 mmol), tetrakis(triphenylphosphine)palladium(0) (24.42 mg, 0.021 mmol), dioxane (1409 μl) and water (705 μl). The reaction 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 (Column: Gemini 150×30 mm, 5 μm, Phenomenex, Torrance, Calif., Flow rate: 40 mL/min, Mobile phase: 0.1% TFA in ACN and water). The fractions containing product were combined and saturated aq. NaHCO3 (15 mL) was added. The aqueous layer was washed with ethyl acetate (1×100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under a vacuum to provide 5-(2-chloro-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (10 mg, 0.021 mmol) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.22 (d, J=8.90 Hz, 1H) 7.36 (dd, J=7.09, 1.03 Hz, 1H) 7.43-7.58 (m, 4H) 7.65 (d, J=7.92 Hz, 1H) 7.85 (s, 1H) 7.99-8.09 (m, 2H) 8.31 (d, J=1.76 Hz, 1H); m/z (ESI) 470 (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. additionThe fractions containing product
  4. additionsaturated aq. NaHCO3 (15 mL) was added
  5. washThe aqueous layer was washed with ethyl acetate (1×100 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under a vacuum

Sources & evidence

ORD record
ord-5b3e9a90a05b41058170e17042a69d20
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09012443B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes