2-Methoxyquinoline → Tert-butyl(2-(2-methoxyquinolin-3-yl)-2-oxoethyl)carbamate

HRID 2205663ノート

反応式

HRID 2205663 の反応式
S(Br)(C)(=O)=O.[Li]C(C)(C)C.[CH3:11][O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.[C:23]([O:27][C:28](=[O:37])[NH:29][CH2:30][C:31](N(OC)C)=[O:32])([CH3:26])([CH3:25])[CH3:24]>C1COCC1.C(Cl)Cl>[C:23]([O:27][C:28](=[O:37])[NH:29][CH2:30][C:31]([C:22]1[C:13]([O:12][CH3:11])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:32])([CH3:26])([CH3:24])[CH3:25]

参加物

7

反応物 4

HCID 1388692-MethoxyquinolineHCID 190026Methanesulfonyl bromideHCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamateHCID 178418306HCID 178418306、化合物

生成物 1

HCID 90149566Tert-butyl(2-(2-methoxyquinolin-3-yl)-2-oxoethyl)carbamate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒4 回

反応条件

温度
-78 °C

実験手順

To a solution of mesyl bromide (17.23 mmol) in 10 mL of THF cooled to −78° C. was added a 1.7 M THF solution of tBuLi (34.5 mmol) dropwise. The mixture was left stirring at −78° C. for 1 h. The mixture was then allowed to reach 0° C. and a solution of 2-methoxyquinoline (12.9 mmol) in THF (40 mL) was added dropwise over 10 min. The resulting mixture was aged at 0° C. for 1 h, cooled to −78° C. and added dropwise with a solution of tert-butyl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate (4.31 mmol) in 20 mL of THF. The mixture was stirred at −78° C. for 30 min then left at room temperature over night. The mixture was diluted with DCM and washed with sat. aq. NaHCO3, dried (Na2SO4), concentrated under reduced pressure and the crude product was purified by flash chromatography (SiO2, Petroleum ether/EtOAc, from 5% to 40% EtOAc). Pooled fractions were concentrated under vacuum to title product (1.01 g). MS (ES) C17H20N2O4 requires: 316.35, found: 317.

後処理

  1. waitThe mixture was left
  2. customto reach 0° C.
  3. waitThe resulting mixture was aged at 0° C. for 1 h
  4. temperaturecooled to −78° C.
  5. stirringThe mixture was stirred at −78° C. for 30 min
  6. waitthen left at room temperature over night
  7. washwashed with sat. aq. NaHCO3
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure
  10. customthe crude product was purified by flash chromatography (SiO2, Petroleum ether/EtOAc, from 5% to 40% EtOAc)
  11. concentrationPooled fractions were concentrated under vacuum to title product (1.01 g)

出典と根拠

ORDレコード
ord-619a52425651405e81622260e8ff2656
出典データセット
uspto-grants-2016_06
特許番号
US09371295B2

反応ノート

読み込み中…