Triethylamine → Tert-butyl 2-methoxy-6-((trimethylsilyl)ethynyl)phenylcarbamate

HRID 1095691Notes

Reaction equation

HRID 1095691 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14].[C:18]([Si:20]([CH3:23])([CH3:22])[CH3:21])#[CH:19].C(N(CC)CC)C>C1COCC1.[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>[CH3:9][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:19]#[C:18][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:3]=1[NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 10760198Tert-butyl 2-iodo-6-methoxyphenylcarbamate

Product 1

HCID 10829462Tert-butyl 2-methoxy-6-((trimethylsilyl)ethynyl)phenylcarbamateYield 98%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl 2-iodo-6-methoxyphenylcarbamate (10.36 g, 29.67 mmol), ethynyltrimethylsilane (3.20 g, 32.63 mmol), copper(I) iodide (0.28 g, 1.48 mmol), and PdCl2(PPh3)2 (1.04 g, 1.48 mmol) in THF (100 mL) was added triethylamine (3.60 g, 35.6 mmol), followed by overnight stirring. The crude reaction was then concentrated and the mixture was flashed through silica gel with 10:1 Hex/EtOAc to give the desired product (98%).

Workup

  1. customThe crude reaction
  2. concentrationwas then concentrated

Sources & evidence

ORD record
ord-07447271bdc54d76b1831bd524957de7
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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