Bromine → HCID 57387326, 화합물

HRID 1800659노트

반응식

HRID 1800659 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([F:30])=[C:13]([NH:15][C:16](=[O:29])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4([C:26]#[N:27])[CH2:25][CH2:24]4)[C:18]=3[Cl:28])[CH:14]=2)=[N:6][CH:7]=1.[S-:31][C:32]#[N:33].[K+].BrBr>C(O)(=O)C>[NH2:33][C:32]1[S:31][C:7]2[C:2]([N:1]=1)=[CH:3][CH:4]=[C:5]([O:8][C:9]1[CH:10]=[CH:11][C:12]([F:30])=[C:13]([NH:15][C:16](=[O:29])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4([C:26]#[N:27])[CH2:24][CH2:25]4)[C:18]=3[Cl:28])[CH:14]=1)[N:6]=2

참가 물질

5

반응물 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 57387083HCID 57387083, 화합물

생성물 1

HCID 57387326HCID 57387326, 화합물수율 69.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution (50 mL) of N-{5-[(5-aminopyridin-2-yl)oxy]-2-fluorophenyl}-2-chloro-3-(1-cyanocyclopropyl)benzamide (4.23 g, 10 mmol) and potassium thiocyanate (3.89 g, 40 mmol) in acetic acid was added dropwise bromine (2.40 g, 15 mmol) at 15° C., and the mixture was stirred at room temperature for 6 hr. The yellow suspension was filtered through celite, and the yellow insoluble material was thoroughly washed with acetic acid (50 mL). The filtrate and washing solution were combined, and the mixture was concentrated under reduced pressure. The residue was suspended in 0.1N aqueous sodium hydroxide solution (100 mL), and the suspension was extracted with ethyl acetate (100 mL). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=100/0→0/100). The obtained residue was crystallized from diethyl ether to give the title compound (3.32 g, 69%) as a pale-yellow powder.

후처리

  1. filtrationThe yellow suspension was filtered through celite
  2. washthe yellow insoluble material was thoroughly washed with acetic acid (50 mL)
  3. washThe filtrate and washing solution
  4. concentrationthe mixture was concentrated under reduced pressure
  5. extractionthe suspension was extracted with ethyl acetate (100 mL)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=100/0→0/100)
  9. customThe obtained residue was crystallized from diethyl ether

출처 및 근거

ORD 기록
ord-f2b03be7e7cf467bad50af9e016b7d3f
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344135B2

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