Toluene → HCID 66995430、化合物

HRID 562922

反応式

HRID 562922 の反応式
C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.[C:14]([C:16]1[CH:17]=[C:18]([C:30]2[CH:31]=[C:32]([CH:37]=[CH:38][N:39]=2)[C:33]([O:35][CH3:36])=[O:34])[CH:19]=[CH:20][C:21]=1OS(C(F)(F)F)(=O)=O)#[N:15].[CH:40]([Si:43]([CH:55]([CH3:57])[CH3:56])([CH:52]([CH3:54])[CH3:53])[N:44]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45]1)([CH3:42])[CH3:41]>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.O>[C:14]([C:16]1[CH:17]=[C:18]([C:30]2[CH:31]=[C:32]([CH:37]=[CH:38][N:39]=2)[C:33]([O:35][CH3:36])=[O:34])[CH:19]=[CH:20][C:21]=1[C:46]1[CH:47]=[CH:48][N:44]([Si:43]([CH:52]([CH3:54])[CH3:53])([CH:55]([CH3:57])[CH3:56])[CH:40]([CH3:41])[CH3:42])[CH:45]=1)#[N:15]

参加物

7

反応物 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27633031-(Triisopropylsilyl)pyrrole-3-boronic acidHCID 86616562HCID 86616562、化合物

生成物 1

HCID 66995430HCID 66995430、化合物収率 5.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

58 mg of tetrakis(triphenylphosphine)palladium and 208 mg of potassium carbonate were added to a toluene (10 ml) solution of 386 mg of methyl 2-(3-cyano-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)isonicotinate and 534 mg of 1-(triisopropylsilyl)pyrrole-3-boronic acid, then this was irradiated with microwaves and heated at 130° C. in a nitrogen atmosphere for 1 hour. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 70:30) to obtain 24 mg of methyl 2-{3-cyano-4-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]phenyl}isonicotinate. (2) 24 mg of this compound was dissolved in 1 ml of THF, and 63 μL of 1 M tetrabutylammonium fluoride/THF solution was added thereto, followed by stirring at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 to 70:30) to obtain 6 mg of methyl 2-[3-cyano-4-(1H-pyrrol-3-yl)phenyl]isonicotinate. (3) 6 mg of this compound was dissolved in a mixture of 0.5 ml of methanol and 0.5 ml of THF, and 22 μl of aqueous 1 M sodium hydroxide solution was added, followed by heating at 60° C. for 2 hours. The reaction liquid was cooled, and the solvent was removed under reduced pressure. Water was added to the residue, followed by neutralization with 1 M hydrochloric acid. The precipitated crystal was collected by filtration and washed with a mixture of ethanol and water to obtain 1.5 mg of 2-[3-cyano-4-(1H-pyrrol-3-yl)phenyl]isonicotinic acid.

後処理

  1. customthis was irradiated with microwaves
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 70:30)

出典と根拠

ORDレコード
ord-42e6bc868a224bd19b8bd3f0f68e6ffa
出典データセット
uspto-grants-2011_11
特許番号
US08067446B2

関連ノート

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