3-Bromopyridine → tert-Butyl (2-oxo-2-(pyridin-3-yl)ethyl)carbamate

HRID 1354402노트

반응식

HRID 1354402 반응식
C([Mg]Br)(C)C.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.COCN[C:17](=[O:27])[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[O:27]=[C:17]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25]

참가 물질

5

반응물 3

HCID 122863-BromopyridineHCID 21105795tert-Butyl {2-[(methoxymethyl)amino]-2-oxoethyl}carbamateHCID 178418365HCID 178418365, 화합물

생성물 1

HCID 58993194tert-Butyl (2-oxo-2-(pyridin-3-yl)ethyl)carbamate수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Isopropylmagnesium bromide (15.5 ml, 2M in THF) was added to a solution of 3-bromopyridine (4.92 g) in THF (30 ml) at 0° C. and stirred for 1 h. A solution of the product from step (a) (2.18 g) in THF (20 ml) was then added and the reaction mixture was stirred at room temperature for 40 h. The mixture was quenched by the addition of saturated ammonium chloride solution (250 ml) and extracted with ethyl acetate. The organic layer was washed with brine and dried (MgSO4). The solvent was evaporated off and the residue purified by chromatography (silica, 20% ethyl acetate/dichloromuethane as eluent) to give the sub-title compound (1.84 g) as a white solid.

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 40 h
  2. customThe mixture was quenched by the addition of saturated ammonium chloride solution (250 ml)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated off
  7. customthe residue purified by chromatography (silica, 20% ethyl acetate/dichloromuethane as eluent)

출처 및 근거

ORD 기록
ord-30105fd64fef4b76bc991af302cdd4fb
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223794B2

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