Bromine → HCID 57779807, 화합물

HRID 552895노트

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HRID 552895 반응식
[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

참가 물질

7

반응물 4

HCID 24408BromineHCID 25517Ammonium ChlorideHCID 57779825HCID 57779825, 화합물HCID 178418339Butyllithium

생성물 1

HCID 57779807HCID 57779807, 화합물수율 33.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

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온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-981020692b9048a0a8c148a8f64d9828
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951951B2

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