Dichloromethane → 5-(5-phenyl-1,3,4-thiadiazol-2-yl)-1-tosyl-1H-indol-3-ylboronic acid

HRID 634239Notes

Reaction equation

HRID 634239 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[S:12][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[N:14][N:15]=3)[CH:9]=2)[N:4]([S:22]([C:25]2[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:3]=1.[B:32]1(B2OC(C)(C)C(C)(C)O2)[O:36]C(C)(C)C(C)(C)[O:33]1.C([O-])(=O)C.[K+].C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.CN(C=O)C>[C:16]1([C:13]2[S:12][C:11]([C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[N:4]([S:22]([C:25]3[CH:26]=[CH:27][C:28]([CH3:29])=[CH:30][CH:31]=3)(=[O:24])=[O:23])[CH:3]=[C:2]4[B:32]([OH:36])[OH:33])=[N:15][N:14]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 683287842-(3-iodo-1-tosyl-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole

Product 1

HCID 683286685-(5-phenyl-1,3,4-thiadiazol-2-yl)-1-tosyl-1H-indol-3-ylboronic acid

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

In a 20 mL microwave tube, a mixture of 2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole (493 mg, 0.884 mmol), bis(pinacolato)diboron (674 mg, 2.65 mmol), potassium acetate (434 mg, 4.42 mmol), PdCl2(dppf), complex with DCM (108 mg, 0.133 mmol) and DMF (4.0 mL) was stirred at 90° C. in the oil bath for 1 h. The mixture was treated with H2O, extracted with EtOAc (50 mL) and washed with brine (2×20 mL), dried over MgSO4, filtered and concentrated affording a brown oil which crystallized upon standing. It was used in the next step without further purification.

Workup

  1. extractionextracted with EtOAc (50 mL)
  2. washwashed with brine (2×20 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customaffording a brown oil which
  7. customcrystallized
  8. customIt was used in the next step without further purification

Sources & evidence

ORD record
ord-1f4b2f7b03864c17ab84222a8e946055
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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