Potassium Carbonate → 2-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]-N-methylacetamide

HRID 1054764

반응식

HRID 1054764 반응식
CO[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:22])=[C:11](B3OCC(C)(C)CO3)[CH:12]=2)[NH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].Br[C:30]1[CH:41]=[CH:40][C:33]([O:34][CH2:35][C:36]([NH:38][CH3:39])=[O:37])=[CH:32][CH:31]=1>>[Cl:22][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([CH:3]=[O:4])=[CH:6][NH:7]2)=[CH:12][C:11]=1[C:30]1[CH:41]=[CH:40][C:33]([O:34][CH2:35][C:36]([NH:38][CH3:39])=[O:37])=[CH:32][CH:31]=1

참가 물질

4

반응물 3

HCID 11430Potassium CarbonateHCID 75350232-(4-bromophenoxy)-N-methylacetamideHCID 86698665methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate

생성물 1

HCID 866987562-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]-N-methylacetamide수율 72.9%

반응 조건

온도
90 °C

실험 절차

To the slurry of methyl-6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (240 mg, 1.0 mmol) was added 2 M potassium carbonate (2.5 mL, 5.0 mmol), 2-(4-bromophenoxy)-N-methylacetamide (240 mg, 1.00 mmol) and PddppfCl2 (50 mg, 0.061 mmol). The sealed vial was heated to 90° C. for 30 min. The reaction was cooled to room temperature and quenched with water (20 mL), and then washed three times with ethyl acetate (20 mL). The combined organics were dried and concentrated to give the title compound (250 mg, 55% yield) as a yellow solid that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 9.94 (s, 1H), 8.37 (d, 1H), 8.02 (s, 1H), 7.68 (s, 1H), 7.38 (d, 2H), 7.05 (d, 2H), 4.52 (s, 2H), 2.68 (d, 3H).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched with water (20 mL)
  3. washwashed three times with ethyl acetate (20 mL)
  4. customThe combined organics were dried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-afc1d5eae2534beeb0de762c66178d6b
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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