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 2223574ノート

反応式

HRID 2223574 の反応式
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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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 (500mg, 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.

後処理

  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

出典と根拠

ORDレコード
ord-21e4a25286724e82bd1929a601427109
出典データセット
uspto-grants-2008_05
特許番号
US07375134B2

反応ノート

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