Trimethylsilylacetylene → Tert-butyl (5-((trimethylsilyl)ethynyl)thiazol-2-yl)carbamate

HRID 2059793Notes

Reaction equation

HRID 2059793 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[N:4][CH:3]=1.[C:15]([Si:17]([CH3:20])([CH3:19])[CH3:18])#[CH:16].C(N(C(C)C)CC)(C)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:18][Si:17]([C:15]#[C:16][C:2]1[S:6][C:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[N:4][CH:3]=1)([CH3:20])[CH3:19]

Participants

7

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 21300388tert-butyl N-(5-bromo-1,3-thiazol-2-yl)carbamate

Product 1

HCID 45117882Tert-butyl (5-((trimethylsilyl)ethynyl)thiazol-2-yl)carbamateYield 86%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl (5-bromo-1,3-thiazol-2-yl)carbamate (2.79 g, 10 mmol), ethynyltrimethylsilane (1.27 g, 13 mmol), Pd(PPh3)4 (578 mg, 0.5 mmol), CuI (143 mg, 0.75 mmol), and diisopropylethylamine (1.94 g, 15 mmol) in DMF (10 mL) was heated at 50° C. overnight under an atmosphere of N2. Upon cooling to ambient temperature, the reaction mixture was concentrated and the crude product was purified by silica gel flash chromatography (eluted with 20% EtOAc/hexanes) to give a yellow solid (2.55 g, 86%).

Workup

  1. temperatureUpon cooling to ambient temperature
  2. concentrationthe reaction mixture was concentrated
  3. customthe crude product was purified by silica gel flash chromatography (eluted with 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fd307c3e74af4021ba605482376db853
Source dataset
uspto-grants-2012_10
Patent number
US08278307B2

Reaction notes

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