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

HRID 1054764

反応式

HRID 1054764 の反応式
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

参加物

4

反応物 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

生成物 1

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

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-afc1d5eae2534beeb0de762c66178d6b
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

関連ノート

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