Sodium Chloride → 2-Amino-3-cyano-4-methyl-5-phenylcarbonylpyridine

HRID 1078244노트

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HRID 1078244 반응식
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5](I)=[CH:4][N:3]=1.[C]=O.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.[Cl-].[Na+].[O:32]1CCOC[CH2:33]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C:33]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:32])=[CH:4][N:3]=1

참가 물질

9

반응물 6

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 113912652-Amino-5-iodo-4-methylnicotinonitrileHCID 178418416HCID 178418416, 화합물3회

생성물 1

HCID 197072072-Amino-3-cyano-4-methyl-5-phenylcarbonylpyridine

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 962Water용매

반응 조건

온도
65 °C

실험 절차

A solution of 4.9 grams (0.019 mole) of 2-amino-3-cyano-5-iodo-4-methylpyridine (prepared as in Step E of Example 9) in 75 mL of dioxane is stirred, and gaseous carbon monoxide is bubbled in during a 15 minute period. While maintaining a carbon monoxide atmosphere, 4.7 grams (0.039 mole) of phenylboronic acid (commercially available), 6.8 mL (0.048 mole) of triethylamine, and 0.5 gram (catalyst) of palladium(11) acetate are in turn added. To maintain the carbon monoxide atmosphere, a balloon filled with carbon monoxide gas is then attached to the reaction vessel. The reaction mixture is then warmed to 65° C. where it is stirred for about 20 hours. The reaction mixture is then poured into a mixture of 300 mL of water and 100 mL of aqueous saturated sodium chloride solution. This mixture is extracted with two 150 mL portions of ethyl acetate. The combined extracts are dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to a residue. The residue is purified using column chromatography, yielding 2-amino-3-cyano-4-methyl-5-phenylcarbonylpyridine.

후처리

  1. customgaseous carbon monoxide is bubbled in during a 15 minute period
  2. additionadded
  3. extractionThis mixture is extracted with two 150 mL portions of ethyl acetate
  4. dry with materialThe combined extracts are dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure to a residue
  7. customThe residue is purified

출처 및 근거

ORD 기록
ord-aec492bf9d124c1290afc042175c25fb
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05547954

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