Bromine → HCID 57779807、化合物

HRID 552895ノート

反応式

HRID 552895 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:16][CH2:17][OH:18])[C:10]2[CH2:14][O:13][C:12](=[O:15])[CH:11]=2)=[CH:4][CH:3]=1.C([Li])CCC.BrBr.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:16][CH2:17][O:18][CH:14]3[O:13][C:12](=[O:15])[CH:11]=[C:10]23)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 24408BromineHCID 25517Ammonium ChlorideHCID 57779825HCID 57779825、化合物HCID 178418339Butyllithium

生成物 1

HCID 57779807HCID 57779807、化合物収率 33.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

At −78° C., a solution of 202 mg (0.75 mmol) of 4-[[(6-chloropyridin-3-yl)methyl](2-hydroxyethyl)-amino]furan-2(5H)-one (II-1) in 7 ml of tetrahydrofuran, also cooled to −78° C., is added to a mixture of 0.6 ml (1.50 mmol) of a 2.5M solution of n-butyllithium in hexane and 3 ml of tetrahydrofuran. After 20 minutes of stirring at −78° C., 39 μl (0.75 mmol) of bromine are added a little at a time, and stirring at −78° C. is continued for a further 30 min. After addition of saturated aqueous ammonium chloride solution, the mixture is warmed to room temperature and extracted with ethyl acetate. The combined organic phase is dried over magnesium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture dichloromethane:methanol (95:5) gives 67 mg (32% of theory) of 1-[(6-chloropyridin-3-yl)methyl]-2,3-dihydro-1H-furo[2,3-b][1,4]oxazin-6(4aH)-one.

後処理

  1. stirringstirring at −78° C.
  2. waitis continued for a further 30 min
  3. temperaturethe mixture is warmed to room temperature
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic phase is dried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm)

出典と根拠

ORDレコード
ord-981020692b9048a0a8c148a8f64d9828
出典データセット
uspto-grants-2011_05
特許番号
US07951951B2

反応ノート

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