2-Chloronicotinoyl chloride → 2-Chloro-N-(2-chloro-6-methyl-4-trifluoromethyl-3-pyridinyl)-3-pyridinecarboxamide

HRID 53515

반응식

HRID 53515 반응식
[NH2:1][C:2]1[C:3]([Cl:13])=[N:4][C:5]([CH3:12])=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C(NC(C)C)(C)C.[Li].[Cl:22][C:23]1[N:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>C1COCC1>[Cl:22][C:23]1[C:24]([C:25]([NH:1][C:2]2[C:3]([Cl:13])=[N:4][C:5]([CH3:12])=[CH:6][C:7]=2[C:8]([F:9])([F:11])[F:10])=[O:26])=[CH:28][CH:29]=[CH:30][N:31]=1

참가 물질

5

반응물 3

HCID 27745412-Chloronicotinoyl chlorideHCID 199600793-Amino-2-chloro-6-methyl-4-(trifluoromethyl)pyridineHCID 45051747Lithium diisopropylamine2회

생성물 1

HCID 199600722-Chloro-N-(2-chloro-6-methyl-4-trifluoromethyl-3-pyridinyl)-3-pyridinecarboxamide수율 72.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a cooled (-78° C.) solution of 2.1 g of the 3-amino-2-chloro-6-methyl-4-(trifluoromethyl)pyridine in 10 ml of THF was added dropwise over 3 min. 7 ml of lithium diisopropylamine (LDA, 1.5 M in cyclohexane). The mixture was stirred 5 min., and 0.9 g of 2-chloronicotinoyl chloride in 3 ml of THF was added over 1 min. After 5 min. an additional 3 ml of LDA solution was added followed by an additional 0.5 g of the acid chloride in 1 ml of THF. The resulting mixture was stirred 10 min. and then quenched with 100 ml of water. After partitioning with 30 ml of ethyl acetate, the organic phase was extracted with water and the combined aqueous phases extracted with methylene chloride, dried (magnesium sulfate), filtered and evaporated to give the crude product. This was washed with a small amount of ethyl acetate and dried to give 1.3 g of the title compound.

후처리

  1. additionwas added dropwise over 3 min
  2. stirringThe resulting mixture was stirred 10 min.
  3. customquenched with 100 ml of water
  4. customAfter partitioning with 30 ml of ethyl acetate
  5. extractionthe organic phase was extracted with water
  6. extractionthe combined aqueous phases extracted with methylene chloride
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. customevaporated
  10. customto give the crude product
  11. washThis was washed with a small amount of ethyl acetate
  12. customdried

출처 및 근거

ORD 기록
ord-94893144c4ff4278af50c60658ae8d42
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620974

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