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Triethylamine → [4-(2-Methoxy-phenylethynyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 1023446
ノート
印刷プレビュー

反応式

HRID 1023446 の反応式
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[C:12](I)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])#[CH:17].CCN(CC)CC>CN(C=O)C.C(OCC)(=O)C.[Cu]I.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:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[C:12]([C:17]#[C:16][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])[CH:11]=[CH:10][N:9]=1)([CH3:4])([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

8

反応物 3

HCID 8471TriethylamineHCID 5829121-Ethynyl-2-methoxybenzeneHCID 11484026(4-Iodo-Pyridin-2-Yl)-Carbamic Acid Tert-Butyl Ester

生成物 1

HCID 69085398[4-(2-Methoxy-phenylethynyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 178418476
HCID 178418476、化合物
触媒
HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of (4-iodo-pyridin-2-yl)-carbamic acid tert-butyl ester (250.0 mg, 0.781 mmol), 1-ethynyl-2-methoxy-benzene (93.8 mg, 0.710 mmol), CuI (13 mg, 0.071 mmol), Pd(PPh3)2Cl2 (25 mg, 0.036 mmol), and Et3N (9 mL) in dry DMF (3 mL) is stirred at room temperature for 19 hours. The reaction is diluted with ethyl acetate (20 mL) and quenched with saturated aqueous NH4Cl (10 mL). The organic layer is washed with an additional portion of saturated aqueous NH4Cl (10 mL), dried over MgSO4, filtered and concentrated. The residue is purified on SiO2 (0-30% ethyl acetate in heptanes, gradient) to give the product.

後処理

  1. customquenched with saturated aqueous NH4Cl (10 mL)
  2. washThe organic layer is washed with an additional portion of saturated aqueous NH4Cl (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified on SiO2 (0-30% ethyl acetate in heptanes, gradient)
  7. customto give the product

出典と根拠

ORDレコード
ord-31ed2e9c0411466eadbbaec9b5b52ee6
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722709B2

反応ノート

読み込み中…

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