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Potassium Carbonate → 4-(4-Methoxybenzyloxy)-8-chloro-7-methoxy-2-(4-methylthiazol-2-yl)quinoline

HRID 388700
ノート
印刷プレビュー

反応式

HRID 388700 の反応式
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][O:8][C:9]2[C:18]3[C:13](=[C:14]([Cl:21])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[N:12]=[C:11](Cl)[CH:10]=2)=[CH:5][CH:4]=1.C([Sn](CCCC)(CCCC)[C:30]1[S:31][CH:32]=[C:33]([CH3:35])[N:34]=1)CCC.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][O:8][C:9]2[C:18]3[C:13](=[C:14]([Cl:21])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[N:12]=[C:11]([C:30]3[S:31][CH:32]=[C:33]([CH3:35])[N:34]=3)[CH:10]=2)=[CH:5][CH:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 164271304-Methyl-2-(tributylstannyl)-1,3-thiazoleHCID 566051532,8-Dichloro-7-methoxy-4-(4-methoxy-benzyloxy)-quinoline

生成物 1

HCID 578167174-(4-Methoxybenzyloxy)-8-chloro-7-methoxy-2-(4-methylthiazol-2-yl)quinoline収率 65%

試薬・触媒・溶媒 2

HCID 178418476
HCID 178418476、化合物
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of compound 274 (1 g, 1 eq.) and 2-(tributylstannyl)-4-methylthiazole (1.28 g, 1.2 eq.) in DMF (14 mL) were added PdCl2(PPh3)2 (193 mg, 10%) and potassium carbonate (455 mg, 1.2 eq.) and the resulting mixture was stirred at 90° C. overnight. DMF was concentrated under vacuum and water and dichloromethane were added. The aqueous layer was extracted with dichloromethane and the combined organic layers washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on a silica gel to yield compound 275 as a white solid in 65% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 2.57 (s, 3H), 3.86 (s, 3H), 4.06 (s, 3H), 5.33 (s, 2H), 6.98 (d, J=8.64 Hz, 2H), 7.08 (s, 1H), 7.25 (d, J=9.25 Hz, 1H), 7.46 (d, J=8.64 Hz, 2H), 7.74 (s, 1H), 8.12 (d, J=9.25 Hz, 1H); MS (ESI, EI+): m/z=427.1 (MH+).

後処理

  1. concentrationDMF was concentrated under vacuum and water and dichloromethane
  2. additionwere added
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washthe combined organic layers washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on a silica gel

出典と根拠

ORDレコード
ord-e2709501c34742fa94b80b2298814654
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08377962B2

反応ノート

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