Water → HCID 68328646, compound

HRID 634248Notes

Reaction equation

HRID 634248 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)O1.[Cl:19][C:20]1[N:24]=[C:23](Cl)[S:22][N:21]=1.O.C([O-])([O-])=O.[K+].[K+]>COCCOC.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>[Cl:19][C:20]1[N:24]=[C:23]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[S:22][N:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2725055Dichloro-1,2,4-thiadiazoleHCID 27347725-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Product 1

HCID 68328646HCID 68328646, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (2 g, 8.23 mmol, Aldrich) and 3,5-dichloro-1,2,4-thiadiazole (1.27 g, 8.23 mmol, Aldrich) in 1,2-dimethoxy ethane (30 mL)/H2O (10 mL) was added K2CO3 (2.27 g, 16.46 mmol) and Pd(PPh3)4 (0.95 g, 0.82 mmol). N2 gas was purged for 15 min through the mixture. The reaction was heated at reflux at 85° C. for 6 h. The mixture was cooled to RT and quenched with H2O (100 mL) and was extracted with EtOAc (2×100 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica-gel column chromatography (eluent: 5% EtOAc in petroleum ether) to give 3-chloro-5-(1H-indol-5-yl)-1,2,4-thiadiazole (680 mg, 35.5%) as an off white solid. MS (ESI, pos. ion) m/z: 236 (M+1); 1H-NMR (300 MHz, CDCl3): δ 8.5 (brs, 1H), 8.29 (d, J=0.8 Hz, 1H), 7.78 (dd, J=8.4, 1.8 Hz, 1H), 7.49 (d, J=8.7 Hz, 1H), 7.32-7.31 (m, 1H), 6.67 (t, J=2.1 Hz, 1H).

Workup

  1. customN2 gas was purged for 15 min through the mixture
  2. temperatureThe reaction was heated
  3. temperatureThe mixture was cooled to RT
  4. customquenched with H2O (100 mL)
  5. extractionwas extracted with EtOAc (2×100 mL)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica-gel column chromatography (eluent: 5% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-8e53c57aa63b452da4f53f07cab1ce30
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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