Potassium Carbonate → N-(2-Hydroxyethyl)-C-[3-(2,4,6-trichlorophenylamino)-phenyl]-methane sulfonamide

HRID 1259041Notes

Reaction equation

HRID 1259041 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][S:9]([NH:12][CH2:13][CH2:14][OH:15])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[C:18]=1Br.C([O-])([O-])=O.[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.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]>[OH:15][CH2:14][CH2:13][NH:12][S:9]([CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:18]2[C:17]([Cl:16])=[CH:22][C:21]([Cl:23])=[CH:20][C:19]=2[Cl:24])[CH:3]=1)(=[O:11])=[O:10]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 1405262-Bromo-1,3,5-trichlorobenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 43256769C-(3-Aminophenyl)-N-(2-hydroxyethyl)-methanesulfonamide

Product 1

HCID 42642570N-(2-Hydroxyethyl)-C-[3-(2,4,6-trichlorophenylamino)-phenyl]-methane sulfonamideYield 5%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

To a stirred solution of C-(3-Aminophenyl)-N-(2-hydroxyethyl)-methanesulfonamide (200 mg, 0.87 mmol), 1,3,5-trichloro-2-bromobenzene (283 mg, 1.09 mmol), K2CO3 (300 mg, 2.17 mmol) and XantPhos (50 mg, 0.09 mmol) in 1,4-dioxane (2 ml) under nitrogen in a microwave tube was added Pd2dba3 (40 mg, 0.04 mmol) in one portion and the tube sealed. The reaction was heated with stirring in a microwave at 150° C. for 60 minutes. The reaction was cooled before filtering through celite. The crude reaction mixture was part-purified by column chromatography eluting with ethyl acetate:hexane and the concentrated fractions further purified by preparative chromatography under acidic conditions to afford the named product (17.8 mg, 5%); 6H (400 MHz, DMSO) 8.00 (1H, s), 7.76 (2H, s), 7.12 (1H, t), 6.99 (1H, t), 6.76 (1H, d), 6.62 (1H, s), 6.48 (1H, d), 4.69 (1H, brs), 4.21 (2H, s), 3.39 (2H, m) and 2.93 (2H, q); LCMS Rt=3.83 min, m/z (ES−) 409 (M−H).

Workup

  1. customthe tube sealed
  2. temperatureThe reaction was heated
  3. temperatureThe reaction was cooled
  4. filtrationbefore filtering through celite
  5. customThe crude reaction mixture
  6. customwas part-purified by column chromatography
  7. washeluting with ethyl acetate
  8. customhexane and the concentrated fractions further purified by preparative chromatography under acidic conditions

Sources & evidence

ORD record
ord-9a74526024e441c4a78d8e67b4c10eea
Source dataset
uspto-grants-2013_06
Patent number
US08466201B2

Reaction notes

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