Potassium Carbonate → 1-[2-(2,6-Dichlorophenylamino)phenyl]-N-[2-(2-hydroxyethoxy)-ethyl]methanesulfonamide

HRID 1259039Notes

Reaction equation

HRID 1259039 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][S:9]([NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18])(=[O:11])=[O:10].[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=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]>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][S:9]([NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18])(=[O:11])=[O:10]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 295681-Bromo-2,6-dichlorobenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 625000681-(2-aminophenyl)-N-[2-(2-hydroxyethoxy)ethyl]methanesulfonamide

Product 1

HCID 426408781-[2-(2,6-Dichlorophenylamino)phenyl]-N-[2-(2-hydroxyethoxy)-ethyl]methanesulfonamide

Reagents, catalysts & solvents 2

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

Conditions

Temperature
160 °C

Procedure

To a stirred solution of 1-(2-aminophenyl)-N-[2-(2-hydroxyethoxy)ethyl]-methanesulfonamide (100 mg, 0.37 mmol), 1,3-dichloro-2-bromobenzene (103 mg, 0.46 mmol), K2CO3 (126 mg, 0.99 mmol) and XantPhos (21 mg, 0.04 mmol) in 1,4-dioxane (2 ml) under nitrogen in a microwave tube was added Pd2dba3 (17 mg, 0.019 mmol) in one portion and the tube sealed. The reaction was heated with stirring in a microwave at 160° C. for 30 minutes. The reaction was cooled before filtering through celite. The crude reaction mixture was purified by column chromatography eluting with ethyl acetate:hexane to afford 1-[2-(2,6-Dichlorophenylamino)phenyl]-N-[2-(2-hydroxyethoxy)-ethyl]methanesulfonamide as product (50.5 mg, 33%); Rf (ethyl acetate:hexane 1:1) 0.11; δH (400 MHz, CDCl3) 7.34 (3H, m), 7.23 (1H, t), 7.19 (1H, s), 7.02 (2H, m), 6.60 (1H, d), 5.70 (1H, s), 4.56 (2H, s), 3.70 (2H, s), 3.56 (4H, m), 3.29 (2H, dt) and 2.83 (1H, s); LCMS Rt=3.97 min, m/z (ES+) 441 (M+Na).

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 purified by column chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-5ff088555c104da2a6f1f498eadb9465
Source dataset
uspto-grants-2013_06
Patent number
US08466201B2

Reaction notes

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