Dimethylformamide → 5-Amino-6-methylpicolinonitrile

HRID 530800

반응식

HRID 530800 반응식
Br[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[CH:4][CH:3]=1.[CH3:10][N:11](C=O)C>CO.O.[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:9][C:5]1[CH:4]=[CH:3][C:2]([C:10]#[N:11])=[N:7][C:6]=1[CH3:8]

참가 물질

7

반응물 2

HCID 6228DimethylformamideHCID 144180456-Bromo-2-methylpyridin-3-amine2회

생성물 1

HCID 552529845-Amino-6-methylpicolinonitrile

시약·촉매·용매 4

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
110 °C

실험 절차

To a solution of 6-bromo-2-methylpyridin-3-amine (compound 1, 500 mg, 2.69 mmol) in DMF (10 mL) was added Zn(CN)2 (943 mg, 8.06 mmol) and Pd(PPh3)4 (288 mg, 0.3 mmol) at room temperature. The reaction was stirred at 110° C. in microwave reactor for 1 h. After it was cooled to room temperature, the mixture was filtered and purified by reverse phase chromatography (X bridge Prep C18OBD, 40-60% MeOH in water with 10 mmol NH4HCO3 modifier) to afford the compound as an oil.

후처리

  1. temperatureAfter it was cooled to room temperature
  2. filtrationthe mixture was filtered

출처 및 근거

ORD 기록
ord-3d0369d5e7464d0e9e0babe420854add
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353104B2

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