Sodium Carbonate → HCID 89923751, compound

HRID 1752652Notes

Reaction equation

HRID 1752652 reaction equation
[Cl:1][C:2]1[N:6]=[C:5](Cl)[S:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:14][N:15]1[C:23]2[C:18](=[CH:19][C:20](B(O)O)=[CH:21][CH:22]=2)[CH:17]=[N:16]1>CN(C=O)C.CCOC(C)=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>[Cl:1][C:2]1[N:6]=[C:5]([C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[N:15]([CH3:14])[N:16]=[CH:17]3)[S:4][N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2725055Dichloro-1,2,4-thiadiazoleHCID 225589101-Methyl-1H-indazole-5-boronic acid

Product 1

HCID 89923751HCID 89923751, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3,5-dichloro-1,2,4-thiadiazole (100 mg, 0.645 mmol), Na2CO3 (0.968 mL, 1.935 mmol) and (1-methyl-1H-indazol-5-yl)boronic acid (114 mg, 0.645 mmol) in DMF (4 mL) was degassed under N2 for 10 min. Pd(Ph3P)4 (149 mg, 0.129 mmol) was added and the mixture was stirred at 80° C. for 2 h. The reaction mixture was cooled to ambient temperature and diluted with EtOAc. The organics were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by preparative TLC (5% MeOH/DCM) to afford the title compound as a solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.12 (s, 3H) 7.50 (d, J=8.79 Hz, 1H) 7.94 (d, J=8.79 Hz, 1H) 8.11 (s, 1H) 8.39 (s, 1H). LC/MS (m/z) ES+=251(M+1).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washThe organics were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC (5% MeOH/DCM)

Sources & evidence

ORD record
ord-4d486ecd2bf14b5da8ea5ae5362fec9e
Source dataset
uspto-grants-2015_10
Patent number
US09163023B2

Reaction notes

Loading…