Dimethylformamide → 5-Amino-6-methylpicolinonitrile

HRID 530800

反応式

HRID 530800 の反応式
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]

参加物

7

反応物 2

HCID 6228DimethylformamideHCID 144180456-Bromo-2-methylpyridin-3-amine2 回

生成物 1

HCID 552529845-Amino-6-methylpicolinonitrile

試薬・触媒・溶媒 4

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-3d0369d5e7464d0e9e0babe420854add
出典データセット
uspto-grants-2016_05
特許番号
US09353104B2

関連ノート

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