Sodium Carbonate → 2-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-benzo[b]thiophene-4-carboxylic acid

HRID 250290ノート

反応式

HRID 250290 の反応式
Br[C:2]1[CH:25]=[CH:24][C:5]([O:6][CH2:7][C:8]2[C:9]([C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:23])=[N:10][O:11][C:12]=2[CH:13]([CH3:15])[CH3:14])=[CH:4][C:3]=1[CH3:26].C(=O)([O-])[O-].[Na+].[Na+].[C:33]([C:36]1[C:44]2[CH:43]=[C:42](B(O)O)[S:41][C:40]=2[CH:39]=[CH:38][CH:37]=1)([OH:35])=[O:34]>O1CCOCC1>[Cl:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=1[C:9]1[C:8]([CH2:7][O:6][C:5]2[CH:24]=[CH:25][C:2]([C:42]3[S:41][C:40]4[CH:39]=[CH:38][CH:37]=[C:36]([C:33]([OH:35])=[O:34])[C:44]=4[CH:43]=3)=[C:3]([CH3:26])[CH:4]=2)=[C:12]([CH:13]([CH3:15])[CH3:14])[O:11][N:10]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 672722084-(4-Bromo-3-methyl-phenoxymethyl)-3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazoleHCID 67272237(4-Carboxybenzo[b]thiophen-2-yl)boronic acid

生成物 1

HCID 580883582-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-benzo[b]thiophene-4-carboxylic acid収率 27.2%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

To a 60° C. suspension of 4-(4-Bromo-3-methyl-phenoxymethyl)-3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazole (0.90 mmol; 410 mg) in a 2M solution of sodium carbonate (7.20 mmol; 3.6 mL) and 1.5 mL of deoxygenated dioxane under a nitrogen atmosphere is slowly added a solution of 4-carboxy-benzo[b]thiophen-2-boronic acid (1.08=mol; 240 mg) in 3.5 mL of deoxygenated dioxane over 1 h via an addition pump. The mixture is stirred for 1 h. The organic solvent is removed under reduced pressure and the residue is acidified with 1N HCl to pH 4. The resulting solution is extracted with dichloromethane. The organic layers are combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue is chromatographed using a gradient from 100% dichloromethane to 100% ethyl acetate to obtain a solid which is washed with acetonitrile to yield the title compound (135 mg, 27%) as a white solid.

後処理

  1. customThe organic solvent is removed under reduced pressure
  2. extractionThe resulting solution is extracted with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed
  7. customto obtain a solid which
  8. washis washed with acetonitrile

出典と根拠

ORDレコード
ord-90bd45e48c0c4cf4ad9d94224a9ffda6
出典データセット
uspto-grants-2011_01
特許番号
US07863302B2

反応ノート

読み込み中…