Sodium Iodide → HCID 58182714, 화합물

HRID 2199615

반응식

HRID 2199615 반응식
[NH2:1][C:2]1[C:9](Br)=[CH:8][C:5](C#N)=[CH:4][N:3]=1.[I-:11].[Na+].CN[C@@H]1CCCC[C@H]1[NH:21][CH3:22]>O1CCOCC1.[Cu]I>[I:11][C:9]1[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([N+:21]#[C-:22])[CH:8]=1

참가 물질

6

반응물 3

HCID 5238Sodium IodideHCID 14912506-Amino-5-bromopyridine-3-carbonitrileHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

생성물 1

HCID 58182714HCID 58182714, 화합물

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

The mixture of 6-amino-5-bromonicotinonitrile (3.315 g, 15.9 mmol, 1 eq), sodium iodide (4.77 g, 2 eq), copper(I) iodide (303 mg, 0.1 eq), and trans-N,N′-dimethylcyclohexane-1,2-diamine (0.52 mL, 0.2 eq) in anhydrous dioxane (40 mL under nitrogen atmosphere was stirred at 120° C. for 20 hours. The mixture was cooled to room temperature then partitioned between ethyl acetate and aqueous ammonium chloride. The organic layer was isolated, further washed with saturated aqueous sodium bicarbonate, brine, and dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated, and the crude solid residue was subject to a column chromatography started first with EtOAc-Hex (1:5 to 1:1) followed by MeOH—CHCl3 (1:100 to 1:20). Product containing fractions were all collected and concentrated. The solid residue was triturated with EtOAc-Hex (1:4) yielding 3-iodo-5-isocyanopyridin-2-amine as an off-white solid in the amount of 2.75 g upon filtration.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customthen partitioned between ethyl acetate and aqueous ammonium chloride
  3. customThe organic layer was isolated
  4. washfurther washed with saturated aqueous sodium bicarbonate, brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe upper solution was decanted
  7. concentrationconcentrated
  8. additionProduct containing fractions
  9. customall collected
  10. concentrationconcentrated
  11. customThe solid residue was triturated with EtOAc-Hex (1:4)

출처 및 근거

ORD 기록
ord-7e1ee5ac571f4c2ca06910a31bacfc15
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359336B2

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