Pyridine → Ethyl 3-{[(benzyloxy)carbonyl]amino}-7-bromo-6-fluoroquinoline-2-carboxylate

HRID 924380ノート

反応式

HRID 924380 の反応式
[NH2:1][C:2]1[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([F:12])=[C:7]([Br:13])[CH:6]=2.N1C=CC=CC=1.Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>C(Cl)Cl.CCOC(C)=O>[CH2:29]([O:28][C:26]([NH:1][C:2]1[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([F:12])=[C:7]([Br:13])[CH:6]=2)=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 86726863Ethyl 3-amino-7-bromo-6-fluoroquinoline-2-carboxylate

生成物 1

HCID 86726865Ethyl 3-{[(benzyloxy)carbonyl]amino}-7-bromo-6-fluoroquinoline-2-carboxylate収率 68%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-10 °C

実験手順

DCM (10.0 mL) was added to a mixture of ethyl 3-amino-7-bromo-6-fluoroquinoline-2-carboxylate (882.5 mg, 2.818 mmol) and pyridine (592.1 mg, 7.485 mmol). The mixture was cooled to −10° C. A solution of benzyl chloroformate (650.6 mg, 3.623 mmol) in DCM (5.0 mL) was added slowly over a period of 5 min. The mixture was then allowed to warm to room temperature and was stirred for 2 h. The reaction mixture was diluted with EtOAc (100 mL), washed with saturated aq. NaHCO3 (100 mL) and brine (100 mL), then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by flash chromatography on silica gel (0-30% EtOAc in hexanes) to give the sub-title compound as an off-white solid (854.9, 68%). LCMS calc. for C20H17BrFN2O4 (M+H)+: m/z=447.0. found 447.0.

後処理

  1. temperatureto warm to room temperature
  2. washwashed with saturated aq. NaHCO3 (100 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by flash chromatography on silica gel (0-30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-aff41ac08d8a4fd8becb9481a10986d5
出典データセット
uspto-grants-2016_03
特許番号
US09278950B2

反応ノート

読み込み中…