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

HRID 1023446
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HRID 1023446 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418476
HCID 178418476, 화합물
촉매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-31ed2e9c0411466eadbbaec9b5b52ee6
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722709B2

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