Dimethylformamide → Methyl 4-(1-cyano-6-methoxynaphthalen-2-yl)benzoate

HRID 1771461ノート

反応式

HRID 1771461 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1.[CH3:24][N:25](C=O)C>[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>[C:24]([C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)#[N:25]

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 67974719Methyl 4-(1-bromo-6-methoxynaphthalen-2-yl)benzoate

生成物 1

HCID 67974370Methyl 4-(1-cyano-6-methoxynaphthalen-2-yl)benzoate収率 82%

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
120 °C

実験手順

To a solution of methyl 4-(1-bromo-6-methoxynaphthalen-2-yl)benzoate (300 mg, 0.811 mmol) (see Example 12 step 1) in DMF (10 mL) was added Zn(CN)2 (191 mg, 1.62 mmol) and Pd(PPh3)4 (93.8 mg, 0.0811 mmol). The resulting mixture was stirred at 120° C. under N2 atmosphere for 16 hours. After cooling to room temperature, the mixture was filtered and the filtrate was diluted with EtOAc (60 mL), washed with H2O (20 mL×3) and brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification by silica gel column (PE/EtOAc=200/1 to 50/1) gave the product (210 mg, yield 82%) as a solid.

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered
  3. additionthe filtrate was diluted with EtOAc (60 mL)
  4. washwashed with H2O (20 mL×3) and brine (20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel column (PE/EtOAc=200/1 to 50/1)

出典と根拠

ORDレコード
ord-be08efcbbab148aea8db41bd3cbceaf6
出典データセット
uspto-grants-2016_02
特許番号
US09249132B2

反応ノート

読み込み中…