Water → HCID 11510487, compound

HRID 1437755Notes

Reaction equation

HRID 1437755 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH3:19])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH:5]=[C:4]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1.O>O1CCOCC1>[F:32][C:33]1[CH:38]=[CH:37][C:36]([C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH3:19])(=[O:17])=[O:16])=[CH:11][CH:10]=3)[CH:5]=[C:4]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:3]=2)=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 11668042HCID 11668042, compound

Product 1

HCID 11510487HCID 11510487, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(6′-chloro-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-2′-ylamino)-N-methyl-benzenesulfonamide (70 mg, 0.18 mmol) in 1,4-dioxane (8 mL) was added sodium carbonate (1N, 80 mg, 0.72 mmol), and tetrakis(triphenyl-phosphine)palladium(0) (21 mg, 0.018 mmol), followed by 4-fluorophenyl boronic acid (49 mg, 0.36 mmol). This reaction was refluxed for 8 hours, after which time water (100 mL) added to the reaction mixture, and the product was extracted with ethyl acetate (100 mL×3). The organic layer was dried over sodium sulphate, filtered, and the filtrate was and concentrated under vacuum. The resulting product was purified through column chromatography using 230-400 mesh silica gel (5% methanol in dichloromethane) to afford the desired compound as A yellow solid (48 mg, Yield 60%). Purity: 98.2%.

Workup

  1. temperatureThis reaction was refluxed for 8 hours
  2. extractionthe product was extracted with ethyl acetate (100 mL×3)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe resulting product was purified through column chromatography

Sources & evidence

ORD record
ord-5fa0d43d80e4483d8063ca0c9f436068
Source dataset
uspto-grants-2009_11
Patent number
US07622486B2

Reaction notes

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