1,4-Dioxane → 4-(2,4-Dimethoxy-benzylamino)-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

HRID 1644626ノート

反応式

HRID 1644626 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[C:4]([F:17])[CH:3]=1.CC(C)([O-])C.[Na+].O1CCOCC1.[CH3:30][O:31][C:32]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:33]=1[CH2:34][NH2:35]>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].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:30][O:31][C:32]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:33]=1[CH2:34][NH:35][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[C:4]([F:17])[CH:3]=1

参加物

7

反応物 4

HCID 312751,4-DioxaneHCID 5972502,4-DimethoxybenzylamineHCID 23676156Sodium t-butoxideHCID 251383534-Bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

生成物 1

HCID 575512544-(2,4-Dimethoxy-benzylamino)-2-fluoro-N-thiazol-2-yl-benzenesulfonamide収率 79.3%

試薬・触媒・溶媒 2

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
100 °C

実験手順

Into a vial was added the 4-bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamide (2.60 g, 0.00771 mol), sodium tert-butoxide (1.78 g, 0.0185 mol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.27 g, 0.00046 mol), tris(dibenzylideneacetone)dipalladium(0) (0.14 g, 0.00015 mol) and 1,4-dioxane (24.1 mL, 0.308 mol). Argon was bubbled for 15 minutes. 2,4-Dimethoxybenzylamine (1.40 mL, 0.00925 mol) was added and the reaction mixture was heated at 100° C. overnight. The reaction mixture was cooled to room temperature then filtered over Celite. The filtrate was concentrated to give the crude product that was purified via automated flash chromatography (silica gel, 50% EtOAc in hexanes to 100% EtOAc) to give the product as a yellow solid (2.59 g, 79.3%).

後処理

  1. customArgon was bubbled for 15 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthen filtered over Celite
  4. concentrationThe filtrate was concentrated
  5. customto give the crude product that
  6. customwas purified

出典と根拠

ORDレコード
ord-69d401905e0b470891e5df3d98f7a9b9
出典データセット
uspto-grants-2012_02
特許番号
US08124610B2

反応ノート

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