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

HRID 1044408

반응식

HRID 1044408 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매2회

실험 절차

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)

후처리

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

출처 및 근거

ORD 기록
ord-febe04c268f74042b1c1e8a49da96f38
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563583B2

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