Potassium Phosphate, Tribasic → HCID 71259332, compound

HRID 1524415Notes

Reaction equation

HRID 1524415 reaction equation
[CH3:1][O:2][C:3]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:4]=1[CH2:5][N:6]([C:29]1[S:33][N:32]=[CH:31][N:30]=1)[S:7]([C:10]1[CH:18]=[C:17]2[C:13]([C:14](B3OC(C)(C)C(C)(C)O3)=[CH:15][N:16]2[CH3:19])=[CH:12][CH:11]=1)(=[O:9])=[O:8].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl:48][C:49]1[CH:54]=[C:53]([C:55]([F:58])([F:57])[F:56])[CH:52]=[CH:51][C:50]=1I>C(OCC)(=O)C.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Cl:48][C:49]1[CH:54]=[C:53]([C:55]([F:56])([F:57])[F:58])[CH:52]=[CH:51][C:50]=1[C:14]1[C:13]2[C:17](=[CH:18][C:10]([S:7]([N:6]([CH2:5][C:4]3[CH:34]=[CH:35][C:36]([O:38][CH3:39])=[CH:37][C:3]=3[O:2][CH3:1])[C:29]3[S:33][N:32]=[CH:31][N:30]=3)(=[O:8])=[O:9])=[CH:11][CH:12]=2)[N:16]([CH3:19])[CH:15]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27366123-Chloro-4-iodobenzotrifluorideHCID 71259251N-(2,4-dimethoxybenzyl)-1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

Product 1

HCID 71259332HCID 71259332, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A vial was charged with N-(2,4-dimethoxybenzyl)-1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (0.500 g, 0.876 mmol), potassium phosphate (0.651 g, 3.07 mmol), and bis(tri-t-butylphosphine)palladium(0) (0.045 g, 0.088 mmol). The vial was flushed with Ar, then 1,4-dioxane (6.57 ml) and water (2.191 ml) were added in sequence, followed by 2-chloro-1-iodo-4-(trifluoromethyl)benzene (0.426 ml, 2.63 mmol). The vial was sealed and stirred at room temperature for two hours. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried with sodium sulfate, filtered and concentrated. The material was purified via column chromatography (RediSep Gold (Teledyne Isco, Lincoln, Nebr.) 40 g, gradient elution 0-100% EtOAc/Heptane) to afford 3-(2-chloro-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (0.405 g, 0.650 mmol, 74.2% yield) as a light yellow solid. m/z (ESI) 624.0 (M+H)+.

Workup

  1. customThe vial was flushed with Ar
  2. addition1,4-dioxane (6.57 ml) and water (2.191 ml) were added in sequence
  3. customThe vial was sealed
  4. washwashed with water
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe material was purified via column chromatography (RediSep Gold (Teledyne Isco, Lincoln, Nebr.) 40 g, gradient elution 0-100% EtOAc/Heptane)

Sources & evidence

ORD record
ord-92f640f46b7244609334f3b5bb58383f
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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