Potassium Carbonate → 4-{3-[2-(Benzhydrylidene-amino)-4-phenyl-quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

HRID 2075663ノート

反応式

HRID 2075663 の反応式
[C:1](=[N:14][C:15]1[CH:24]=[C:23](Cl)[C:22]2[C:17](=[CH:18][C:19]([S:26][C:27]3[CH:28]=[C:29]([C:33]4([C:39]#[N:40])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH:30]=[CH:31][CH:32]=3)=[CH:20][CH:21]=2)[N:16]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:41]1(B(O)O)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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:1](=[N:14][C:15]1[CH:24]=[C:23]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:22]2[C:17](=[CH:18][C:19]([S:26][C:27]3[CH:28]=[C:29]([C:33]4([C:39]#[N:40])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH:30]=[CH:31][CH:32]=3)=[CH:20][CH:21]=2)[N:16]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 866138264-{3-[2-(Benzhydrylidene-amino)-4-chloro-quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

生成物 1

HCID 866138274-{3-[2-(Benzhydrylidene-amino)-4-phenyl-quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

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
90 °C

実験手順

1r (100 mg, 0.18 mmol), phenylboronic acid (26 mg, 0.21 mmol), Pd(PPh3)4 (20 mg, 0.02 mmol), and potassium carbonate (50 mg, 0.36 mmol) was dissolved in 1,4-dioxane and water and degassed with N2. The mixture was heated to 90° C. until no starting material was seen by tlc analysis. The reaction was cooled to room temperature, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the desired product, 1s.

後処理

  1. customwater and degassed with N2
  2. temperatureThe reaction was cooled to room temperature
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-01adbc05cbf84216b961eb1c119e7a24
出典データセット
uspto-grants-2011_04
特許番号
US07919621B2

反応ノート

読み込み中…