Cesium carbonate → [4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}thio)phenyl]boronic acid

HRID 2423536노트

반응식

HRID 2423536 반응식
Cl[CH2:2][C:3]1[C:4]([C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[N:5][O:6][C:7]=1[CH:8]([CH3:10])[CH3:9].C(=O)([O-])[O-].[Cs+].[Cs+].[SH:25][C:26]1[CH:31]=[CH:30][C:29]([B:32]([OH:34])[OH:33])=[CH:28][CH:27]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[C:4]1[C:3]([CH2:2][S:25][C:26]2[CH:31]=[CH:30][C:29]([B:32]([OH:34])[OH:33])=[CH:28][CH:27]=2)=[C:7]([CH:8]([CH3:10])[CH3:9])[O:6][N:5]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 44318944-Mercaptophenylboronic acidHCID 592648754-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazole

생성물 1

HCID 59321491[4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}thio)phenyl]boronic acid수율 131.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

A mixture of 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole (152 mg, 0.5 mmol), cesium carbonate (489 mg, 1.5 mmol) and 4-mercaptophenyl boronic acid (75 mg, 0.5 mmol) in dimethylformamide (5 mL) was allowed to stir for 24 hours in a 60° C. oil bath. The mixture was diluted with ethyl acetate and washed with water. The organic layer was washed with brine, dried with magnesium sulfate, filtered and concentrated to yield 277 mg of crude [4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}thio)phenyl]boronic acid and dimethylformamide. 1H NMR (400 MHz, d6-DMSO): δ 7.63-7.59 (m, 4H), 7.55-7.51 (m, 1H), 7.17 (d, J=8 Hz, 2H), 3.86 (s, 2H), 3.12 (septet, J=7 Hz, 1H), 1.13 (d, J=7 Hz, 6H).

후처리

  1. washwashed with water
  2. washThe organic layer was washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-640dbdae7d2846bcb1aaa1bae87b82f7
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960552B2

반응 노트

불러오는 중…