Ammonium Chloride → (6-chloropyridin-3-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone

HRID 626272ノート

反応式

HRID 626272 の反応式
I[C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)=[CH:4][CH:3]=1.C([Li])CCC.[Cl:20][C:21]1[CH:32]=[CH:31][C:24]([C:25](N(OC)C)=[O:26])=[CH:23][N:22]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:20][C:21]1[N:22]=[CH:23][C:24]([C:25]([C:2]2[CH:14]=[CH:13][C:5]([O:6][CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][O:8]3)=[CH:4][CH:3]=2)=[O:26])=[CH:31][CH:32]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 29168032H-Pyran, tetrahydro-2-(4-iodophenoxy)-HCID 114355976-Chloro-N-methoxy-N-methylnicotinamideHCID 178418339Butyllithium

生成物 1

HCID 89655790(6-chloropyridin-3-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone収率 66.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

2-(4-Iodophenoxy)tetrahydro-2H-pyran (18.2 g, 59.9 mmol) was dissolved in 100 mL dry tetrahydrofuran and cooled to −78° C. under nitrogen atmosphere, and then n-butyllithium was added dropwise to the solution. After addition, the solution was stirred at −78° C. for 0.5 h, 6-chloro-N-methoxy-N-methylnicotinamide (8.0 g, 39.9 mmol) in 50 mL tetrahydrofuran was added dropwise and keep the temperature under −78° C. for 2 h. Then 100 mL of aqueous saturated ammonium chloride was added. The mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate, concentrated in vacuo, and purified by column chromatography to give the desired product as a yellow solid (8.4 g, 66.3%).

後処理

  1. additionAfter addition
  2. customunder −78° C.
  3. customfor 2 h
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography

出典と根拠

ORDレコード
ord-245bc76d81f1407194bb18726e7edb97
出典データセット
uspto-grants-2016_04
特許番号
US09309211B2

反応ノート

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