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Toluene → 4-[8-(4-Methylsulfanyl-phenyl)quinolin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester

HRID 1864181
ノート
印刷プレビュー

反応式

HRID 1864181 の反応式
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:23]3[C:18](=[C:19](Cl)[CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH3:25][S:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C(OCC)(=O)C.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>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:23]3[C:18](=[C:19]([C:30]4[CH:31]=[CH:32][C:27]([S:26][CH3:25])=[CH:28][CH:29]=4)[CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 574963804-(8-Chloro-quinolin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester

生成物 1

HCID 114079414-[8-(4-Methylsulfanyl-phenyl)quinolin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 8857Ethyl Acetate溶媒

実験手順

In a 25 mL round-bottomed flask equipped with a reflux condenser and N2 inlet septum was placed a stir bar, 4-(8-chloro-quinolin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester (198 mg, 0.57 mmol), 4-methylthiophenylboronic acid (287 mg, 1.7 mmol), tetrakis(triphenylphosphine)palladium (98 mg, 0.085 mmol), 2M sodium carbonate (0.6 mL) and toluene (4 mL). The mixture was refluxed 36 h under N2. The resulting mixture was diluted with ethyl acetate and extracted with H2O. The organic extract was dried and concentrated to give the crude product. The crude product was purified by column chromatography to using 50% EtOAc/Hexane and preparative HPLC to give the desired product. 1H NMR (CDCl3, 400MHz) δ 1.27 (d, 6H), 2.04 (m, 2H), 2.17 (m, 2H), 2.55 (s, 3H), 3.59 (m, 2H), 3.83 (m, 2H), 4.97 (m, 1H), 5.09 (m, 1H), 7.14 (s, 1H), 7.41 (m, 4H), 7.81 (t, 1H), 7.90 (d, 1H), 8.38 (d, 1H), 9.11 (s, 1H). Exact mass calculated for C25H28N2O3S 436.18, found 437.2 (MH+).

後処理

  1. customIn a 25 mL round-bottomed flask equipped with a reflux condenser and N2 inlet septum
  2. temperatureThe mixture was refluxed 36 h under N2
  3. extractionextracted with H2O
  4. extractionThe organic extract
  5. customwas dried
  6. concentrationconcentrated
  7. customto give the crude product
  8. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-d7372beef36a4a96bc7d9061cd4615c8
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07625906B2

反応ノート

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