ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
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
  1. ホーム
  2. /反応

Dichloromethane → 1-(3-Fluoro-5-(6-methoxynaphthalen-2-yl)pyridin-4-yl)ethanol

HRID 1897576
ノート
印刷プレビュー

反応式

HRID 1897576 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](B(O)O)[CH:7]=[CH:6]2.Br[C:17]1[CH:18]=[N:19][CH:20]=[C:21]([F:26])[C:22]=1[CH:23]([OH:25])[CH3:24].C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:26][C:21]1[CH:20]=[N:19][CH:18]=[C:17]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]=2)[C:22]=1[CH:23]([OH:25])[CH3:24]
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 6344DichloromethaneHCID 10340Sodium CarbonateHCID 46416926-Methoxy-2-naphthaleneboronic acidHCID 699379091-(3-Bromo-5-Fluoro-pyridin-4-yl)-ethanol

生成物 1

HCID 699373971-(3-Fluoro-5-(6-methoxynaphthalen-2-yl)pyridin-4-yl)ethanol収率 51%

試薬・触媒・溶媒 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 6-methoxynaphthalen-2-ylboronic acid (333 mg, 1.650 mmol), 1-(3-bromo-5-fluoropyridin-4-yl)ethanol 4a (330 mg, 1.5 mmol), sodium carbonate (2M in water, 1.5 mL, 3.00 mmol), PdCl2(dppf).CH2Cl2 adduct (61.2 mg, 0.075 mmol) in DMF (6 mL) was heated to 100° C. for 2 hrs. The mixture was quenched with sat NaHCO3 and extracted with EtOAc two times, dried over magnesium sulfate, filtered, concentrated. The residue was purified via Biotage (20-60% EtOAc/heptane; SNAP25 column) giving the title compound (227 mg, 51%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.62 (dd, J=6.7, 1.0 Hz, 3H), 3.96 (s, 3H), 4.99 (q, J=6.7 Hz, 1H), 7.19-7.26 (m, 2H), 7.36 (dd, J=8.4, 1.7 Hz, 1H), 7.70 (s, 1H), 7.78 (d, J=8.9 Hz, 1H), 7.83 (d, J=8.5 Hz, 1H), 8.40 (s, 1H), 8.48 (d, J=2.7 Hz, 1H). LC-MS (M+1) 298.0, t=1.49 min.

後処理

  1. customThe mixture was quenched with sat NaHCO3
  2. extractionextracted with EtOAc two times
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via Biotage (20-60% EtOAc/heptane; SNAP25 column)

出典と根拠

ORDレコード
ord-5527eace12414eaf8eef5e23bf530026
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08519134B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート