Triethylamine → 4-Ethyl-5-trimethylsilanylethynyl-thiazol-2-ylamine

HRID 1009039Notes

Reaction equation

HRID 1009039 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([NH2:9])[S:6][C:7]=1I)[CH3:2].C(N(CC)CC)C.[C:17]([Si:19]([CH3:22])([CH3:21])[CH3:20])#[CH:18].[NH4+].[Cl-]>C(#N)C.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>[CH2:1]([C:3]1[N:4]=[C:5]([NH2:9])[S:6][C:7]=1[C:18]#[C:17][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 866309544-Ethyl-5-iodo-thiazol-2-ylamine

Product 1

HCID 866309554-Ethyl-5-trimethylsilanylethynyl-thiazol-2-ylamine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

Under a stream of Ar the above prepared 4-ethyl-5-iodo-thiazol-2-ylamine (1.67 g, 6.57 mmol) was dissolved in 40 mL of acetonitrile and treated successively with triethylamine (2.73 mL, 3 eq.), Cul (0.125 g, 0.1 eq.), (Ph3P)2PdCl2 (0.46 g, 0.1 eq.) and ethynyltrimethylsilane (2.73 mL, 3 eq.). The flask was closed with a septum and allowed to stir for 15 h at ambient temperature. The reaction mixture was then poured onto icewater/NH4Cl, twofold extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=7/3) afforded finally 0.598 g of the title compound as brown viscous oil, contaminated with some des-iodo-compound.

Workup

  1. customThe flask was closed with a septum
  2. extractiontwofold extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-42b8e34bc556430c8bba6efc986a3565
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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