Potassium Hydroxide → HCID 72190829, compound

HRID 1487057Notes

Reaction equation

HRID 1487057 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:4][C:3]=1[S:16]([N:19]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=1[CH3:31])[CH2:20][CH:21]([CH3:23])[CH3:22])(=[O:18])=[O:17].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.[OH-:62].[K+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:31][C:25]1[CH:26]=[C:27]([CH3:30])[CH:28]=[CH:29][C:24]=1[N:19]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:16]([C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:7][C:2]=1[OH:62])(=[O:18])=[O:17]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 72190830HCID 72190830, compound

Product 1

HCID 72190829HCID 72190829, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

2-chloro-N-(2,4-dimethylphenyl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide (200 mg, 0.429 mmol), tris(dibenzylideneacetone)dipalladium(0) (3.93 mg, 4.29 μmol), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (1.822 mg, 4.29 μmol) and potassium hydroxide (72.2 mg, 1.287 mmol) were added to a microwave vial. The reactants where dissolved in 1,4-dioxane (1.2 mL) and water (1.2 mL). The reaction vessel was sealed and heated by microwaves (Biotage Initiator) to 150° C. for 2 hours. The reaction mixture was concentrated in vacuo, 2N NaOH was added and the reaction was diluted with ethyl acetate. The organic phase was separated and was washed with 2N HCl. The organic phase was separated, dried using a hydrophobic frit and evaporated in vacuo to give the crude product as a yellow oil. The crude was purified by mass directed autoprep (ammonium carbonate modifier). The relevant fractions were then concentrated under a stream of nitrogen to give the required product, 32 mg. LCMS [LCMS2] Rt 1.51 min, m/z (ES+) 448 (M+H).

Workup

  1. customThe reaction vessel was sealed
  2. concentrationThe reaction mixture was concentrated in vacuo, 2N NaOH
  3. additionwas added
  4. additionthe reaction was diluted with ethyl acetate
  5. customThe organic phase was separated
  6. washwas washed with 2N HCl
  7. customThe organic phase was separated
  8. customdried
  9. customevaporated in vacuo
  10. customto give the crude product as a yellow oil
  11. customThe crude was purified by mass
  12. concentrationThe relevant fractions were then concentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-f25bb00dadb84c2bb8ab85d6447acfeb
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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