Triethylamine → HCID 25258327, compound

HRID 505804Notes

Reaction equation

HRID 505804 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][C:3]=1[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[CH3:20][Si:21]([C:24]#[CH:25])([CH3:23])[CH3:22].CCN(CC)CC>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>[C:16]([O:15][C:13]([NH:12][C:3]1[CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:6][C:2]=1[C:25]#[C:24][Si:21]([CH3:23])([CH3:22])[CH3:20])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 25258089HCID 25258089, compound

Product 1

HCID 25258327HCID 25258327, compoundYield 70%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
50 °C

Procedure

A solution (0.1 M) of ethyl 5-bromo-4-[(tert-butoxycarbonyl)amino]thiophene-2-carboxylate in THF was treated with trimethylsilylacetylene (1.3 eq.), Et3N (1.5 eq.), CuI (0.04 eq.) and PdCl2(PPh3)2 (0.01 eq.). The solution was heated at 50° C. for 3 h. After cooling down, it was filtered through a pad of celite and washed with AcOEt. The organic layer was washed with brine and dried then concentrated and the residue was purified by flash chromatography on silica gel (1:19 AcOEt/petroleum ether) to afford the title compound (70%) as a solid.

Workup

  1. temperatureAfter cooling down
  2. filtrationit was filtered through a pad of celite
  3. washwashed with AcOEt
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationthen concentrated
  7. customthe residue was purified by flash chromatography on silica gel (1:19 AcOEt/petroleum ether)

Sources & evidence

ORD record
ord-66d6c5e0b11b415faad8faf8bb432bd5
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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