Triethylamine → HCID 11851001, compound

HRID 2299907Notes

Reaction equation

HRID 2299907 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:23]1([C:29]#[CH:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:30]#[C:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 2773612tert-butyl N-(4-iodophenyl)carbamate

Product 1

HCID 11851001HCID 11851001, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Iodo-phenyl)-carbamic acid tert-butyl ester (2.0 g, 6.27 mmol) was dissolved in THF (50 mL), treated with triethylamine (4.4 mL, 31.4 mmol), phenylacetylene (1.03 mL, 9.40 mmol), cuprous iodide (0.06 g, 0.31 mmol), and Pd(Ph3)2Cl2 (0.44 g, 0.63 mmol). The reaction was stirred overnight, then filtered and concentrated. The crude material was chromatographed on silica gel eluting with 7:1 hexane/EtOAc to give 1.48 g (80%) of the desired product.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe crude material was chromatographed on silica gel eluting with 7:1 hexane/EtOAc

Sources & evidence

ORD record
ord-0fc4b617b39a497e8dae44aa92057cb7
Source dataset
uspto-grants-2002_12
Patent number
US06495715B2

Reaction notes

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