Potassium Phosphate, Tribasic → N-[5-[4-(5-{[4-(1-Methylethyl)-1-piperazinyl]methyl}-1,3,4-oxadiazol-2-yl)-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide

HRID 520521Notes

Reaction equation

HRID 520521 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([C:20]2[O:21][C:22]([CH2:25][N:26]3[CH2:31][CH2:30][N:29]([CH:32]([CH3:34])[CH3:33])[CH2:28][CH2:27]3)=[N:23][N:24]=2)[CH:3]=1.[CH3:35][O:36][C:37]1[C:42]([NH:43][S:44]([CH3:47])(=[O:46])=[O:45])=[CH:41][C:40](B2OC(C)(C)C(C)(C)O2)=[CH:39][N:38]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:33][CH:32]([N:29]1[CH2:30][CH2:31][N:26]([CH2:25][C:22]2[O:21][C:20]([C:4]3[CH:3]=[C:2]([C:40]4[CH:41]=[C:42]([NH:43][S:44]([CH3:47])(=[O:45])=[O:46])[C:37]([O:36][CH3:35])=[N:38][CH:39]=4)[CH:10]=[C:9]4[C:5]=3[CH:6]=[N:7][N:8]4[S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])=[N:24][N:23]=2)[CH2:27][CH2:28]1)[CH3:34]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 59564698N-(2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methanesulfonamideHCID 667764806-bromo-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3,4-oxadiazol-2-yl)-1-(phenylsulfonyl)-1H-indazole

Product 1

HCID 66695774N-[5-[4-(5-{[4-(1-Methylethyl)-1-piperazinyl]methyl}-1,3,4-oxadiazol-2-yl)-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamideYield 100%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-bromo-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3,4-oxadiazol-2-yl)-1-(phenylsulfonyl)-1H-indazole (100 mg, 0.183 mmol) in 1,4-dioxane (2.5 ml) and water (0.250 ml) was added N-[2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]methanesulfonamide (78 mg, 0.238 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride (26.8 mg, 0.037 mmol) and potassium phosphate tribasic (117 mg, 0.550 mmol). The mixture was heated under microwave irradiation at 60° C. for 10 min, then the solvent was removed in vacuo and the residue partitioned between dichloromethane (5 ml) and water (5 ml), separated by hydrophobic frit and purified by silica (5 g) cartridge using a gradient of dichloromethane and methanol to give the title compound as a brown solid (122 mg).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue partitioned between dichloromethane (5 ml) and water (5 ml)
  3. customseparated by hydrophobic frit
  4. custompurified by silica (5 g) cartridge

Sources & evidence

ORD record
ord-15fbc37cc91a4e4d9208c3fc82cd69f8
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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