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

HRID 659969

반응식

HRID 659969 반응식
[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]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 1362742,2-Difluoroethanamine2회HCID 216982012-Chloro-5-(chloromethyl)-3-fluoropyridine

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fd3210e947094643a320aad6d69415e6
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084452B2

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