Ammonium Chloride → 4-{3-Chloro-4-[2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-ethyl]-phenoxy}-benzonitrile

HRID 1095901ノート

反応式

HRID 1095901 の反応式
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH3:13])[CH:8]=1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:27]=[CH:28][C:29]=1[CH:30]([CH3:33])[CH:31]=[O:32])[O:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1.[NH4+].[Cl-]>CCCCCC.C1COCC1>[Cl:14][C:15]1[CH:16]=[C:17]([CH:27]=[CH:28][C:29]=1[CH:30]([CH3:33])[CH:31]([OH:32])[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH3:13])[CH:8]=1)[O:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 27628354-Bromo-2-methylpyridineHCID 866459484-[3-Chloro-4-(1-methyl-2-oxo-ethyl)-phenoxy]-benzonitrileHCID 178418339Butyllithium

生成物 1

HCID 666990954-{3-Chloro-4-[2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-ethyl]-phenoxy}-benzonitrile

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

A 1.6 M solution of n-BuLi in hexane (1.05 ml) was added to 4-bromo-2-methylpyridin (CAS Reg. No. 22282-99-1, 289 mg) in THF (5 ml) at −78° C. The deep red solution was stirred for 10 min. A solution of 4-[3-chloro-4-(1-methyl-2-oxo-ethyl)-phenoxy]-benzonitrile (400 mg) in THF (5 ml) was added at −78° C. The mixture was allowed to warm to 0° C. and stirred for 15 min at that temperature. Saturated aqueous NH4Cl solution was added and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2) to give the title compound (200 mg) as a light yellow solid. MS (m/e)=379.2 [M+H+].

後処理

  1. customat −78° C
  2. stirringstirred for 15 min at that temperature
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated to an oil
  6. customThe residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2)

出典と根拠

ORDレコード
ord-983d7a252dbc4b11ba07c243f588774c
出典データセット
uspto-grants-2012_03
特許番号
US08138189B2

反応ノート

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