Sodium Carbonate → 4-(4-Fluorophenyl)-7-methyl-2-quinolinecarbonitrile

HRID 922750ノート

反応式

HRID 922750 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]#[N:14])[CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>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.O1CCOCC1>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=3)[N:5]=[C:4]([C:13]#[N:14])[CH:3]=2)=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 597749194-Chloro-7-methylquinoline-2-carbonitrile

生成物 1

HCID 574378434-(4-Fluorophenyl)-7-methyl-2-quinolinecarbonitrile収率 85.9%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

4-Chloro-7-methylquinoline-2-carbonitrile (1-5, 2.47 g, 12.2 mmol, 1.0 equiv.), 4-fluorophenylboronic acid (2.05 g, 14.63 mmol, 1.2 equiv.), Pd(PPh3)4 (0.7 g, 0.61 mmol, 0.05 equiv), and 1M aqueous Na2CO3 (12.2 ml, 2.39 mmol) was added into 1,4-dioxane (40 mL). The mixture was degassed and stirred at 100° C. for 16 hours, until disappearance of the starting material. The mixture was cooled, saturated aqueous sodium hydrogen carbonate (2 mL) was added and the mixture was extracted with ethyl acetate (2×50 mL). The combined organic fractions were washed with brine, dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was treated with 50 ml of MeOH, stirred vigorously at rt for 1 h, the mixture was filtered and washed with MeOH. The solid was collected and dried under vacuum. The filtrate was concentrated and retreated with MeOH to get a second crop of white solid that was combined to the first to give 2.75 g of 4-(4-fluorophenyl)-7-methylquinoline-2-carbonitrile (1-6). LRMS m/z (M+H)+ 263.3 found, 263.3 required.

後処理

  1. customThe mixture was degassed
  2. temperatureThe mixture was cooled
  3. additionsaturated aqueous sodium hydrogen carbonate (2 mL) was added
  4. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. additionThe residue was treated with 50 ml of MeOH
  10. stirringstirred vigorously at rt for 1 h
  11. filtrationthe mixture was filtered
  12. washwashed with MeOH
  13. customThe solid was collected
  14. customdried under vacuum
  15. concentrationThe filtrate was concentrated
  16. customto get a second crop of white solid

出典と根拠

ORDレコード
ord-1fa4a12661894ea8a84d8cd447818399
出典データセット
uspto-grants-2016_03
特許番号
US09278960B2

反応ノート

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