1,2-Dibromobenzene → [(4-Bromo-phenyl)-thiazol-2-yl-methyl]-[3-methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-amine

HRID 1009306노트

반응식

HRID 1009306 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Br:8].[Li]CCCC.[CH3:14][CH:15]([CH3:34])[CH2:16][CH:17]([N:27]=[CH:28][C:29]1[S:30][CH:31]=[CH:32][N:33]=1)[C:18]12[O:25][CH2:24][C:21]([CH3:26])([CH2:22][O:23]1)[CH2:20][O:19]2>CCOCC>[Br:8][C:3]1[CH:4]=[CH:5][C:6]([CH:28]([NH:27][CH:17]([C:18]23[O:25][CH2:24][C:21]([CH3:26])([CH2:22][O:23]2)[CH2:20][O:19]3)[CH2:16][CH:15]([CH3:34])[CH3:14])[C:29]2[S:30][CH:31]=[CH:32][N:33]=2)=[CH:7][CH:2]=1

참가 물질

5

반응물 3

HCID 114141,2-DibromobenzeneHCID 67298572[3-Methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-thiazol-2-ylmethyleneamineHCID 178418339Butyllithium

생성물 1

HCID 67298665[(4-Bromo-phenyl)-thiazol-2-yl-methyl]-[3-methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-amine

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of dibromobenzene (760 mg, 3.2 mmol) in dry ether was added 2.5 M solution of nBuLi in hexanes (1.3 mL, 3.2 mmol) at −30° C. After stirring for 1 h, a solution of [3-methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-thiazol-2-ylmethylene-amine (500 mg, 1.6 mmol) in 5 mL of dry ether was added slowly. The reaction mixture was allowed to stir at the same temperature for 2 h and then the reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with saturated NaCl and dried over MgSO4. The solvent was evaporated in vacuo. The crude was flash column chromatographed using 2:1 hexanes:EtOAc as an eluant to get [(4-bromo-phenyl)-thiazol-2-yl-methyl]-[3-methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-amine as a pale yellow solid.

후처리

  1. stirringto stir at the same temperature for 2 h
  2. customthe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated NaCl
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated in vacuo
  7. customchromatographed

출처 및 근거

ORD 기록
ord-27b14a6e1f8f4e5baad1ccef22992aaa
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973037B2

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