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

HRID 1259041ノート

反応式

HRID 1259041 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9a74526024e441c4a78d8e67b4c10eea
出典データセット
uspto-grants-2013_06
特許番号
US08466201B2

反応ノート

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