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

HRID 1023446Notes

Reaction equation

HRID 1023446 reaction equation
[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]

Participants

8

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-31ed2e9c0411466eadbbaec9b5b52ee6
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

Loading…