Triethylamine → HCID 15735939, compound

HRID 889071Notes

Reaction equation

HRID 889071 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]([C:12]1[S:13][C:14](Br)=[CH:15][CH:16]=1)=[O:11].[CH2:18]([OH:22])[CH2:19][C:20]#[CH:21]>[Pd](Cl)Cl.[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(#N)C>[CH3:8][O:9][C:10]([C:12]1[S:13][C:14]([C:21]#[C:20][CH2:19][CH2:18][OH:22])=[CH:15][CH:16]=1)=[O:11]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 135663-Butyn-1-OL2×HCID 605713Methyl 5-bromothiophene-2-carboxylate

Product 1

HCID 15735939HCID 15735939, compound

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24290Palladium ChlorideCatalystHCID 83717Copper iodideCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

To a 20-mL vial for microwave reaction, were added a mixture of palladium chloride (57 mg, 0.32 mmol), triphenylphosphine (104 mg, 0.32 mmol), copper iodide (243 mg, 1.28 mmol), triethylamine (8.08 g, 80 mmol), 5-bromo-thiophene-2-carboxylic acid methyl ester (1.77 g, 8 mmol) and anhydrous acetonitrile (10 mL). To the stirred mixture, were added copper iodide (243 mg, 1.28 mmol) and but-3-yn-1-ol, 1 (588 mg, 8.4 mmol), and the vial was sealed and put into the microwave reactor at 100° C. for 10 min. After evaporation of solvent under reduced pressure, MeOH (20 mL) was added followed by silica gel (5 g). The resulting plug was loaded on to a silica gel column (3.5×12 cm) and eluted with hexane followed by 20% EtOAc in hexane. Fractions with an Rf=0.42 (hexane/EtOAc 4:1) were pooled and evaporated to afford 1.17 g of 2 as yellow oil. 1H NMR (DMSO-d6): δ 2.59-2.63 (t, J=6.4 Hz, 2H), 3.56-3.59 (t, J=6.4 Hz, 2H), 3.81 (s, 3H), 4.95-4.98 (t, J=5.6 Hz, 1H), 7.27-7.28 (d, J=4.0 Hz, 1H), 7.69-7.70 (d, J=4.0 Hz, 1H).

Workup

  1. customTo a 20-mL vial for microwave reaction
  2. additionwere added
  3. customthe vial was sealed
  4. customAfter evaporation of solvent under reduced pressure, MeOH (20 mL)
  5. additionwas added
  6. washeluted with hexane
  7. customevaporated

Sources & evidence

ORD record
ord-f3fee1dfe027445b87fd962af026b979
Source dataset
uspto-grants-2012_08
Patent number
US08252804B2

Reaction notes

Loading…