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Lithium Hydroxide → 3-(3-(1-Naphthyloxy)propyl)-5-((1e)-3-phenylprop-1-enyl)-1h-indole-2-carboxylic acid

HRID 1013277
ノート
印刷プレビュー

反応式

HRID 1013277 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13]CC)=[O:12])=[C:5]2[CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.[C:30]1([CH2:36]/[CH:37]=[CH:38]/B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Li+].[OH-]>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>[C:20]1([O:19][CH2:18][CH2:17][CH2:16][C:5]2[C:9]3[C:8](=[CH:4][CH:3]=[C:2](/[CH:38]=[CH:37]/[CH2:36][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:10]=3)[NH:7][C:6]=2[C:11]([OH:13])=[O:12])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 3939Lithium HydroxideHCID 11041016trans-3-Phenylpropen-1-yl-boronic acidHCID 67315656Ethyl 5-bromo-(3-(3-(naphthalen-1-yloxy)propyl))-1h-indole-2-carboxylate

生成物 1

HCID 251002793-(3-(1-Naphthyloxy)propyl)-5-((1e)-3-phenylprop-1-enyl)-1h-indole-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 178418476HCID 178418476、化合物
触媒

実験手順

A mixture of EXAMPLE 11C (45.2 mg), (E)-3-phenylprop-1-enylboronic acid (21.1 mg), bis(triphenylphosphine)palladium(II) dichloride (catalytic), and 2M LiOH (0.3 mL) in 7/2/3dimethoxyethane/ethanol/H2O (2 mL) was heated under microwave (CEM Discover) conditions at 150° C. for 30 minutes. The mixture was quenched with 1 MHCl (0.4 mL) and extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated. The cruconcentrate was purified by reverse phase HPLC (Zorbax SB-C18, 20-100% acetonitrile/water/0.1% trifluoroacetic acid). 1H NMR (500 MHz, DMSO-d6) δ 12.95 (brs, 1H), 11.44 (s, 1H), 8.34 (d, 1H), 7.88 (d, 1H), 7.54 (m, 2H), 7.44 (m, 2H), 7.31 (m, 5H), 7.18 (m, 3H), 6.83 (d, 1H), 6.00 (m, 2H), 4.08 (t, 2H), 2.21 (m, 2H).

後処理

  1. customThe mixture was quenched with 1 MHCl (0.4 mL)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe cruconcentrate was purified by reverse phase HPLC (Zorbax SB-C18, 20-100% acetonitrile/water/0.1% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-961b7270754d4af89a52057cb9f4e59b
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07981888B2

反応ノート

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