2-Bromo-5-chloropyridine → HCID 178451146、化合物

HRID 2207376ノート

反応式

HRID 2207376 の反応式
[Li]C(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1.[C:14]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])[CH2:19][CH2:18]1)(=[O:16])[CH3:15]>C(Cl)Cl>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:14]([C@H:17]2[CH2:22][CH2:21][C@H:20]([C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])[CH2:19][CH2:18]2)([OH:16])[CH3:15])=[N:8][CH:9]=1

参加物

5

反応物 3

HCID 8170982-Bromo-5-chloropyridineHCID 178418306HCID 178418306、化合物HCID 178451155HCID 178451155、化合物

生成物 1

HCID 178451146HCID 178451146、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

t-BuLi (0.950 mL, 1.52 mmol) was added dropwise to a cooled solution of 2-bromo-5-chloropyridine (225 mg, 1.17 mmol) in DCM (11 mL) at −78° C. over 2 minutes. The reaction mixture was stirred for 2 hours at −78° C. and a solution of butyl trans-4-acetylcyclohexanecarboxylate (291 mg, 1.286 mmol) in DCM (1 mL) was added dropwise at −78° C. The reaction mixture was slowly warmed to room temperature over a period of 16 hours. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with DCM (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to afford trans-butyl 4-(1-(5-chloropyridin-2-yl)-1-hydroxyethyl)cyclohexanecarboxylate as a brown oil. MS ESI calc'd for C18H27ClNO3 [M+H]+ 340. found 340.

後処理

  1. temperatureThe reaction mixture was slowly warmed to room temperature over a period of 16 hours
  2. customThe reaction mixture was quenched with saturated aqueous NH4Cl
  3. extractionextracted with DCM (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-1084353c6071462ca758614fd7cc31a9
出典データセット
uspto-grants-2016_06
特許番号
US09376418B2

反応ノート

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