Triethylamine → S-3304

HRID 1617285

Reaction equation

HRID 1617285 reaction equation
Br[C:2]1[S:6][C:5]([S:7]([NH:10][C@H:11]([CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[C:12]([OH:14])=[O:13])(=[O:9])=[O:8])=[CH:4][CH:3]=1.[C:25]1([CH3:33])[CH:30]=[CH:29][C:28]([C:31]#[CH:32])=[CH:27][CH:26]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.[Cu]I>[NH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([CH2:15][C@@H:11]([NH:10][S:7]([C:5]2[S:6][C:2]([C:32]#[C:31][C:28]3[CH:29]=[CH:30][C:25]([CH3:33])=[CH:26][CH:27]=3)=[CH:3][CH:4]=2)(=[O:9])=[O:8])[C:12]([OH:14])=[O:13])=[CH:17]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 13018p-EthynyltolueneHCID 11396269(R)-2-(5-Bromo-thiophene-2-sulfonylamino)-3-(1H-indol-3-yl)-propionic acid

Product 1

HCID 10718956S-3304Yield 55.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

In a round bottom flask was added crude (R)-2-(5-Bromo-thiophene-2-sulfonylamino)-3-(1H-indol-3-yl)-propionic acid (3) (60 mg, 0.14 mmol), p-tolyl acetylene 4 (480 mg, 0.41 mmol), PdCl2P(PPh3)2 (10 mg, 0.015 mmol), copper(I)iodide (2 mg, 0.01 mmol) and triethylamine (0.025 g, 0.25 mmol) and then dissolved in dry DMF (2 mL) under an atmosphere of nitrogen. The reaction mixture was then heated at 50° C. under a nitrogen atmosphere for 2 hours. The reaction mixture was then cooled to room temperature and diluted with ethyl acetate and washed with a solution composed of NaCl/NaHCO3/(NH4)2CO3/water (1:1:1:1) (×3), water, and then dried over sodium sulfate (Na2SO4). The crude product was purified using a SAX column to provide to give the desired (R)-3-(1H-Indol-3-yl)-2-(5-p-tolylethynyl-thiophene-2-sulfonylamino)-propionic acid 5 (0.036 g, 55%).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. washwashed with a solution
  3. dry with materialdried over sodium sulfate (Na2SO4)
  4. customThe crude product was purified
  5. customto provide

Sources & evidence

ORD record
ord-2b120fd0b58f4976bcf5c3117d058314
Source dataset
uspto-grants-2014_07
Patent number
US08765953B2

Linked notes

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