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

HRID 1771461노트

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HRID 1771461 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

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온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-be08efcbbab148aea8db41bd3cbceaf6
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249132B2

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