Water → 4-bromo-2-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

HRID 1627329노트

반응식

HRID 1627329 반응식
[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:3]=1[CH2:4][S:5][C:6]1[N:7]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:8]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)([CH3:13])[CH3:12])=[CH:9][N:10]=1.C(=O)([O-])[O-].[Na+].[Na+].O.[Br:41]Br>C(Cl)Cl>[Br:41][C:9]1[N:10]=[C:6]([S:5][CH2:4][C:3]2[C:29]([F:33])=[CH:30][CH:31]=[CH:32][C:2]=2[Cl:1])[N:7]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:8]=1[C:11]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)([CH3:13])[CH3:12]

참가 물질

6

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24408BromineHCID 469086492-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

생성물 1

HCID 866622414-bromo-2-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (950 mg, 1.81 mmol) and sodium carbonate (634 mg, 5.98 mmol) in DCM:H2O (5 mL:5 mL) was added bromine (0.1 mL, 2.00 mmol) dropwise at 0° C. The resulting mixture was stirred for 3 h and diluted with DCM (15 mL). The organic layer was washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The crude material was purified with flash chromatography to afford the title compound (970 mg, 89%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.62 (s, 6H), 4.35 (s, 2H), 6.43 (m, 2H), 6.80 (t, 2H), 6.84 (dd, 1H), 6.95 (t, 1H), 6.99 (dd, 1H), 7.16 (m, 2H), 7.25 (t, 1H); MS (EI) m/z 602 [M+H]+.

후처리

  1. washThe organic layer was washed with H2O and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified with flash chromatography

출처 및 근거

ORD 기록
ord-bad940ed5b6e4017b958e7b0c4db23d7
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785488B2

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