Phosphorus oxychloride → tert-Butyl 6-bromo-3',6'-dihydro-2,4'-bipyridine-1'(2'H)-carboxylate

HRID 403198ノート

反応式

HRID 403198 の反応式
[Br:1][C:2]1[N:7]=[C:6]([C:8]2(O)[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 86614831tert-Butyl 4-(6-bromopyridin-2-yl)-4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 86614830tert-Butyl 6-bromo-3',6'-dihydro-2,4'-bipyridine-1'(2'H)-carboxylate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

To a solution of tert-butyl 4-(6-bromopyridin-2-yl)-4-hydroxypiperidine-1-carboxylate (100 mg) in pyridine (2.5 ml) is added, at 0° C. under argon, POCl3 (0.26 ml). The mixture is stirred at 0° C. and then slowly warmed to room temperature. The mixture is stirred at room temperature overnight. The reaction mixture is subsequently admixed with saturated sodium hydrogencarbonate solution and the aqueous phase is removed. After the aqueous phase has been extracted with tert-butyl methyl ether, the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The residue is purified by chromatography. This gives tert-butyl 6-bromo-3′,6′-dihydro-2,4′-bipyridine-1′(2′H)-carboxylate (60 mg).

後処理

  1. temperatureslowly warmed to room temperature
  2. stirringThe mixture is stirred at room temperature overnight
  3. customthe aqueous phase is removed
  4. extractionAfter the aqueous phase has been extracted with tert-butyl methyl ether
  5. dry with materialthe combined organic phases are dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by chromatography

出典と根拠

ORDレコード
ord-e2d965447b0e49699427a2bb749675df
出典データセット
uspto-grants-2014_06
特許番号
US08748420B2

反応ノート

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