2-Methyl-2-butene → 6-chloro-5-[4-[2-(methylamino)-2-oxoethoxy]phenyl]-1H-indole-3-carboxylic acid

HRID 1054765ノート

反応式

HRID 1054765 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:24]=[CH:23][C:16]([O:17][CH2:18][C:19]([NH:21][CH3:22])=[O:20])=[CH:15][CH:14]=1.CC(=CC)C.Cl([O-])=[O:31].[Na+].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>C(#N)C.C(O)(C)(C)C.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:31])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]([NH:21][CH3:22])=[O:20])=[CH:23][CH:24]=1

参加物

7

反応物 4

HCID 105532-Methyl-2-buteneHCID 24243Trisodium PhosphateHCID 23668197Sodium ChloriteHCID 866987562-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]-N-methylacetamide

生成物 1

HCID 866987576-chloro-5-[4-[2-(methylamino)-2-oxoethoxy]phenyl]-1H-indole-3-carboxylic acid収率 47.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 22050040Acetonitrile tert-butanol溶媒

反応条件

温度
0 °C

実験手順

To a mixture of 2-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]-N-methylacetamide (120 mg, 0.35 mmol) in acetonitrile/t-butanol (4 mL/4 mL) was added 2-methyl-2-butene (4 mL). The reaction mixture was cooled to 0° C. followed by the addition of an aqueous solution of sodium chlorite (630 mg, 7.00 mmol) and sodium phosphate (monobasic and monohydrate, 930 mg, 7.00 mmol) in water (5 mL) dropwise via additional funnel. The ice bath was removed and the reaction was stirred at room temperature overnight. The reaction was quenched with sodium sulfite. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by pre-HPLC to give the title compound (60 mg, 47% yield) as a white solid. MS (ES+) 359.0 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 12.12 (s, 1H), 11.94-11.93 (m, 1H), 8.07 (d, 2H), 7.92 (s, 1H), 7.62 (s, 1H), 7.37 (d, 2H), 7.04 (d, 2H), 4.52 (s, 2H), 2.68 (d, 3H).

後処理

  1. customThe ice bath was removed
  2. customThe reaction was quenched with sodium sulfite
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe resulting residue was purified by pre-HPLC

出典と根拠

ORDレコード
ord-bb08ff01798f445d98d14956f78f6b05
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

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