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

HRID 1054765

반응식

HRID 1054765 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 22050040Acetonitrile tert-butanol용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bb08ff01798f445d98d14956f78f6b05
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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