Nitrogen → 4-(2-Phenyleth-1-ynyl)thiophene-2-carbaldehyde

HRID 1363250Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1.N#N.[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(NC(C)C)(C)C.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.[Cu](I)I>[C:11]1([C:17]#[C:18][C:2]2[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Under a N2 atmosphere, 4-bromothiophene-2-carbaldehyde (1.0 g, 5.2 mmol) was taken up in diisopropylamine (20 mL). TPP (549 mg, 2.1 mmol), bis(benzonitrile)palladium chloride ([Pd(PhCN)2]Cl2) (400 mg, 1.0 mmol), and copper iodide (199 mg, 1.0 mmol) were added. The mixture was degassed with N2 before phenylacetylene (1.15 mL, 10.4 mmol) was added, and the reaction was stirred at 70° C. for 16 h. The mixture was concentrated to a dark brown solid and chromatographed in 0-15% EtOAc in heptane to yield 4-(phenylethynyl)thiophene-2-carbaldehyde (981 mg, 88%). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.93 (d, 1H), 7.88 (t, 1H), 7.85 (d, 1H), 7.53 (m, 2H), 7.38 (m, 3H).

Workup

additionwas added
concentrationThe mixture was concentrated to a dark brown solid
customchromatographed in 0-15% EtOAc in heptane

Sources & evidence

ORD record: ord-0c28c548d6ce41eab751f5073a9f5344
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884124B2

Reaction notes

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