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

HRID 1473292Notes

Reaction equation

HRID 1473292 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+].[CH3:34][N:35]1[C:39](B(O)O)=[CH:38][CH:37]=[N:36]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:39]2[N:35]([CH3:34])[N:36]=[CH:37][CH:38]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 11182610(1-methyl-1H-pyrazol-5-yl)boronic acidHCID 866873495-(2-Bromo-4-chlorophenyl)-N-(1,2,4-thiadiazol-5-YL)naphthalene-2-sulfonamide

Product 1

HCID 866873515-(4-chloro-2-(1-methyl-1H-pyrazol-5-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), (1-methyl-1H-pyrazol-5-yl)boronic acid (84 mg, 0.666 mmol), tetrakis(triphenylphosphine)palladium(0) (19.23 mg, 0.017 mmol), dioxane (1109 μl) and water (555 μl). The reaction was heated in a microwave at 100° C. for 30 min. The resulting mixture was concentrated and purified by reverse phase HPLC (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 a white solid 5-(4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (5 mg, 0.01 mmol). 1H NMR (500 MHz, DMSO-d6) δ ppm 3.48 (s, 3H) 7.01 (s, 1H) 7.05 (d, J=1.82 Hz, 1H) 7.11 (s, 1H) 7.21 (s, 1H) 7.43 (d, J=6.41 Hz, 1H) 7.49 (d, J=8.55 Hz, 1H) 7.53-7.64 (m, 3H) 7.64-7.75 (m, 3H) 8.11 (d, J=8.23 Hz, 1H) 8.34 (s, 1H) 8.43 (d, J=1.60 Hz, 1H); m/z (ESI) 482.0 (M+H)+.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. custompurified by reverse phase HPLC (Column: Xbridge 19×100 mm, 5 μm, Waters, Milford, Mass., Flow rate: 40 mL/min, Mobile phase: 0.1% TFA in ACN and water)
  3. additionThe fractions containing product
  4. customwere dried under a vacuum

Sources & evidence

ORD record
ord-073d787ee56f4aed98fdc07479ba1197
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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