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

HRID 1009045Notes

Reaction equation

HRID 1009045 reaction equation
I[C:2]1[S:6][C:5]([NH2:7])=[N:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[C:21]([Si:23]([CH3:26])([CH3:25])[CH3:24])#[CH:22].[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>[C:8]1([C:3]2[N:4]=[C:5]([NH2:7])[S:6][C:2]=2[C:22]#[C:21][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 866309575-Iodo-4-phenyl-thiazol-2-ylamine

Product 1

HCID 866309584-Phenyl-5-trimethylsilanylethynyl-thiazol-2-ylamine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

Under a stream of Ar the above prepared 5-iodo-4-phenyl-thiazol-2-ylamine (1.60 g, 5.29 mmol) was dissolved in 30 mL of acetonitrile and treated successively with triethylamine (2.09 mL, 3 eq.), Cul (0.096 g, 0.1 eq.), (Ph3P)2PdCl2 (0.353 g, 0.1 eq. and ethynyltrimethylsilane (2.09 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/ethyl acetate=8/2) yielded finally 1.075 g of the title compound as brown foam. MS (ISP): 273.3 [M+H]+.

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-27a1a383add84e06ad90e3fb5442abca
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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