Potassium Carbonate → 5-(2-Bromo-4-chlorophenyl)-N-(1,2,4-thiadiazol-5-YL)naphthalene-2-sulfonamide

HRID 1473291Notes

Reaction equation

HRID 1473291 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+].Br[C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH:27]=[CH:28][C:29]([S:35]([N:38](CC1C=CC(OC)=CC=1OC)[C:39]1[S:43][N:42]=[CH:41][N:40]=1)(=[O:37])=[O:36])=[CH:30]2>O1CCOCC1.O.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>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH:27]=[CH:28][C:29]([S:35]([NH:38][C:39]1[S:43][N:42]=[CH:41][N:40]=1)(=[O:37])=[O:36])=[CH:30]2

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 866873455-bromo-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide2×HCID 866873502-(2-Bromo-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 866873495-(2-Bromo-4-chlorophenyl)-N-(1,2,4-thiadiazol-5-YL)naphthalene-2-sulfonamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A pressure vessel was charged with 2-(2-bromo-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.732 g, 2.306 mmol), potassium carbonate (1.328 g, 9.61 mmol), 5-bromo-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (Intermediate D) (1 g, 1.922 mmol), tetrakis(triphenylphosphine)palladium(0) (0.222 g, 0.192 mmol) in dioxane (12.81 mL) and water (6.41 mL). The reaction was heated in an oil bath at 100° C. for 35 min. LC/MS indicated that the desired product (M+H=479.8) was generated. Water was added to the mixture and washed with EtOAc. The water layer was acidified with 5% HCl (15 mL) and washed with EtOAc again to afford a light yellow solid. The product was used in the next reaction without further purification. m/z (ESI) 480.0 (M+H)+.

Sources & evidence

ORD record
ord-0d19d8e53f8a4862b8b7edb3451106fb
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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