Triethylamine → HCID 21083103, compound

HRID 490021Notes

Reaction equation

HRID 490021 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:16]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)#[CH:17]>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.[Cu]I.C1COCC1>[I:8][C:5]1[CH:6]=[CH:7][C:2]([C:17]#[C:16][C:18]2[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 12208p-DiiodobenzeneHCID 37600254-Ethynylaniline2×

Product 1

HCID 21083103HCID 21083103, compoundYield 354.1%

Reagents, catalysts & solvents 3

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

Procedure

1,4-Diiodobenzene (4.95 g, 1.0 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.070 g, 0.10 mmol), copper(I) iodide (0.019 g, 0.10 mmol), triethylamine (5 mL), THF (10 mL) and 4-ethynylaniline 0.585 g, 5.00 mmol) were used following the general procedure for couplings. For the synthesis of 4-ethynylaniline, please see Tour et al. Chem. Eur. J. 2001, vol. 7, pp. 5118-5134 incorporated herein by reference. The tube was capped and stirred room temperature for 12 h. Flash column chromatography (CH2Cl2—hexanes as eluent) afforded the desired product as light yellow needles (1.13 g, 71% yield). IR (KBr) 3441, 3356, 2210, 1612, 1515, 1281, 1135, 1003, 842, 811, 512 cm−1. 1H NMR (400 MHz, CDCl3) δ7.650 (m, AA′ part of AA‘XX’ pattern, J=8.7, 2.4, 1.8, 0.7 Hz, 2H), 7.324 (m, XX′ part of AA′XX′ pattern, J=8.7, 2.4, 1.8, 0.7 Hz, 2H), 7.208 (m, AA′ part of AA′XX′ pattern, J=8.6, 2.4, 1.8, 0.6 Hz, 2H), 6.630 (m, XX′ part of AA′XX′ pattern, J=8.6, 2.4, 1.8, 0.6 Hz, 2H), 3.833 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 147.05, 137.60, 133.20, 133.07, 123.67, 114.95, 112.39, 93.45, 91.83, 86.69.

Workup

  1. customThe tube was capped

Sources & evidence

ORD record
ord-a644f2565aec45988e51953c9e35ac4f
Source dataset
uspto-grants-2009_05
Patent number
US07527831B2

Reaction notes

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