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

HRID 1354402ノート

反応式

HRID 1354402 の反応式
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]

参加物

5

反応物 3

HCID 122863-BromopyridineHCID 21105795tert-Butyl {2-[(methoxymethyl)amino]-2-oxoethyl}carbamateHCID 178418365HCID 178418365、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-30105fd64fef4b76bc991af302cdd4fb
出典データセット
uspto-grants-2007_05
特許番号
US07223794B2

反応ノート

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