2-Methyl-2-butene → HCID 86698614、化合物

HRID 338267ノート

反応式

HRID 338267 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20]2)=[CH:15][CH:14]=1.CC(=CC)C.Cl([O-])=[O:37].[Na+].O.O.OP([O-])(O)=O.[Na+]>C(#N)C.C(O)(C)(C)C.O>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][CH:19]([C:16]2[CH:17]=[CH:18][C:13]([C:3]3[CH:4]=[C:5]4[C:9](=[CH:10][C:2]=3[Cl:1])[NH:8][CH:7]=[C:6]4[C:11]([OH:37])=[O:12])=[CH:14][CH:15]=2)[CH2:20]1)=[O:25])([CH3:30])([CH3:29])[CH3:28]

参加物

8

反応物 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium Chlorite2 回HCID 23673460Sodium Phosphate, Monobasic, Dihydrate2 回HCID 86698613HCID 86698613、化合物

生成物 1

HCID 86698614HCID 86698614、化合物収率 36.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒HCID 6386tert-Butanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of tert-butyl 3-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenyl]pyrrolidine-1-carboxylate (43 mg, 0.1 mmol) in acetonitrile (1.2 mL) and tert-butanol (1.2 mL) was added 2-methyl-2-butene (1.2 mL). The reaction mixture was cooled to 0° C. and treated with a solution of sodium chlorite (100 mg, 1.1 mmol) and sodium phosphate monobasic dihydrate (234 mg, 1.5 mmol) in water (0.6 mL). After the resulting mixture was stirred for 2 h at room temperature, additional sodium chlorite (134 mg, 1.47 mmol) and sodium phosphate monobasic dihydrate (312 mg, 2.0 mmol) in H2O (0.6 mL) was added to the reaction mixture. The resulting mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the aqueous residue was extracted with EtOAc (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in DMSO and purified via pre-HPLC to give 5-{4-[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]phenyl}-6-chloro-1H-indole-3-carboxylic acid (16 mg, 36%) as a white solid. MS (ES+) 463.1 (M+Na)+.

後処理

  1. stirringThe resulting mixture was stirred at room temperature for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionthe aqueous residue was extracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in DMSO
  7. custompurified via pre-HPLC

出典と根拠

ORDレコード
ord-98861d3dd7a7405b8462918843a19a90
出典データセット
uspto-grants-2014_11
特許番号
US08889730B2

反応ノート

読み込み中…