Potassium Carbonate → HCID 118060468, compound

HRID 2274844Notes

Reaction equation

HRID 2274844 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][NH:23][CH:24]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.[Cl:25][C:26]1[N:27]=[N:28][C:29]([Cl:33])=[CH:30][C:31]=1Cl.C([O-])([O-])=O.[K+].[K+]>CC#N.CCOC(C)=O>[Cl:25][C:26]1[N:27]=[N:28][C:29]([Cl:33])=[CH:30][C:31]=1[N:23]1[CH:24]=[C:20]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[N:8]([S:11]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)(=[O:12])=[O:13])[CH:7]=2)[CH:21]=[N:22]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 951233,4,6-TrichloropyridazineHCID 1180601346-fluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole2×

Product 1

HCID 118060468HCID 118060468, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 6-fluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole (Intermediate 5; 200 mg; 0.59 mmol) in MeCN (10 mL) was added 3,4,6-trichloropyridazine (97 mg; 0.529 mmol) and K2CO3 (146 mg; 1.06 mmol) under nitrogen. The mixture was stirred at 85° C. for 24 hours, diluted with EtOAc (100 mL), washed with water (50 mL×3), brine (50 mL), dried over anhydrous Na2SO4, filtered, concentrated, and purified by reversed phase flash chromatography to afford 100 mg (39%) of the title compound a the yellow solid.

Workup

  1. washwashed with water (50 mL×3), brine (50 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by reversed phase flash chromatography

Sources & evidence

ORD record
ord-0cea9d9c025f4ed6b365ae9a6f0f4865
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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