Triethylamine → N-[(6-chloro-5-fluoropyridin-3-yl)methyl]-2,2-difluoroethylamine

HRID 659969

反応式

HRID 659969 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][C:3]=1[F:10].[F:11][CH:12]([F:15])[CH2:13][NH2:14].C(N(CC)CC)C>C(#N)C.Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:14][CH2:13][CH:12]([F:15])[F:11])=[CH:4][C:3]=1[F:10]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 1362742,2-Difluoroethanamine2 回HCID 216982012-Chloro-5-(chloromethyl)-3-fluoropyridine

生成物 1

HCID 86639346N-[(6-chloro-5-fluoropyridin-3-yl)methyl]-2,2-difluoroethylamine収率 57%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6342Acetonitrile溶媒

実験手順

At 45° C., 520 mg (2.89 mmol) of 6-chloro-3-chloromethyl-5-fluoropyridine (VII-3), 1.05 ml (14.44 mmol) of 2,2-difluoroethylamine and 400 μL (2.89 mmol) of triethylamine are stirred in 50 ml of acetonitrile for about 48 hours. After about 16 and 32 hours, in each case another 0.42 ml (5.78 mmol) of 2,2-difluoroethylamine are added. After concentration of the reaction mixture under reduced pressure, the residue is taken up in 1 N aqueous hydrochloric acid and the mixture is washed with ethyl acetate. The aqueous phase is made alkaline using 2.5 N aqueous sodium hydroxide solution and extracted repeatedly with ethyl acetate. The combined organic phase is dried over sodium sulphate and concentrated under reduced pressure, giving 370 mg (57% of theory) of N-[(6-chloro-5-fluoropyridin-3-yl)methyl]-2,2-difluoroethylamine.

後処理

  1. washthe mixture is washed with ethyl acetate
  2. extractionextracted repeatedly with ethyl acetate
  3. dry with materialThe combined organic phase is dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-fd3210e947094643a320aad6d69415e6
出典データセット
uspto-grants-2011_12
特許番号
US08084452B2

関連ノート

読み込み中…