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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
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2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 1-(6-(3,5-Dichloro-4-hydroxyphenyl)-4-(4-((dimethylamino)methyl)phenylamino)quinolin-3-yl)ethanone

HRID 2271791
ノート
印刷プレビュー

反応式

HRID 2271791 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=1.[Cl:26][C:27]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[C:29]([Cl:42])[C:28]=1[OH:43]>ClCCl.CO>[Cl:26][C:27]1[CH:32]=[C:31]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]3[NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH3:24])[CH3:25])=[CH:18][CH:17]=2)[CH:30]=[C:29]([Cl:42])[C:28]=1[OH:43]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 667157981-(6-Bromo-4-(4-((dimethylamino)methyl)phenylamino)quinolin-3-yl)ethanone

生成物 1

HCID 682985471-(6-(3,5-Dichloro-4-hydroxyphenyl)-4-(4-((dimethylamino)methyl)phenylamino)quinolin-3-yl)ethanone収率 122.7%

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

実験手順

Following general procedure F, 1-(6-bromo-4-(4-((dimethylamino)methyl)phenylamino)quinolin-3-yl)ethanone (2.0 g, 5.09 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (2.2 g, 7.6 mmol) to obtain the free base. The purified product was suspended in dichloromethane/methanol (1:1, 40 mL) and HBr gas was bubbled through the suspension until a solution formed. The solution was concentrated to dryness and the resultant solid was triturated with diethyl ether. The mixture was filtered, washed with diethyl ether, and dried to obtain desired product (3.0 g, 94% over two steps) as a yellow solid: 1H NMR (300 MHz, DMSO) δ 11.93 (s, 1H), 10.59 (s, 1H), 9.81 (s, 1H), 9.24 (s, 1H), 8.37 (m, 2H), 8.11 (d, J=8.8 Hz, 1H), 7.66 (d, J=8.5 Hz, 2H), 7.56 (s, 2H), 7.51 (d, J=8.5 Hz, 2H), 4.39 (d, J=4.0 Hz, 2H), 2.74 (d, J=4.0 Hz, 6H), 2.54 (s, 3H). APCI MS m/z 480 [C26H23Cl2N3O2+H]+; HPLC>99% (AUC), tR=4.79 min.

後処理

  1. customto obtain the free base
  2. customHBr gas was bubbled through the suspension until a solution
  3. customformed
  4. concentrationThe solution was concentrated to dryness
  5. customthe resultant solid was triturated with diethyl ether
  6. filtrationThe mixture was filtered
  7. washwashed with diethyl ether
  8. customdried

出典と根拠

ORDレコード
ord-74d32fa1e0614a13b9c4ef999e6ee605
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09120749B2

反応ノート

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