Pyridine → 4-chloro-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one

HRID 1044408

反応式

HRID 1044408 の反応式
N1C=CC=CC=1.[Cl:7][C:8]1[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=1.[OH:15][C:16]([CH3:31])([CH3:30])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][C:20]=1[O:28][CH3:29]>C(Cl)Cl.CO>[Cl:7][C:8]1[CH:13]=[CH:12][N:11]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH2:17][C:16]([OH:15])([CH3:31])[CH3:30])=[C:20]([O:28][CH3:29])[CH:21]=2)[C:10](=[O:14])[CH:9]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 27576114-Chloropyridin-2-olHCID 585798634-(2-Hydroxy-2-methylpropoxy)-3-methoxyphenylboronic acid

生成物 1

HCID 585802944-chloro-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one収率 62.8%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

Pyridine (1.2 mL, 15.4 mmol) was added to a stirred solution of commercially available 4-chloropyridin-2(1H)-one (100 mg, 0.77 mmol), 4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenylboronic acid Part C (278 mg, 1.16 mmol), and copper (II) acetate, monohydrate (154 mg, 0.77 mmol) in CH2Cl2 (7 mL) and MeOH (0.7 mL). The reaction mixture stirred at RT under the presence of air overnight (21 hours). The reaction mixture was diluted with CH2Cl2, washed with IN HCl, sat. NaHCO3, dried (Na2SO4), and concentrated. The crude product was purified using preparative HPLC (C18 column/10:90:0.1 to 90:10:0.1 MeOH—H2O-TFA) to afford the desired product 4-chloro-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one 9D (169 mg, 0.49 mmol, 62.8% yield) as a brown gum. LC/MS 324 (M+H)+, tR 0.75 min (method 5)

後処理

  1. washwashed with IN HCl, sat. NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified

出典と根拠

ORDレコード
ord-febe04c268f74042b1c1e8a49da96f38
出典データセット
uspto-grants-2013_10
特許番号
US08563583B2

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