Triethylamine → 3-((Trimethylsilyl)ethynyl)benzamide

HRID 705751Notes

Reaction equation

HRID 705751 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[Si:37]([C:41]#[CH:42])([CH3:40])([CH3:39])[CH3:38]>C1COCC1.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>[CH3:38][Si:37]([C:41]#[C:42][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6])([CH3:40])[CH3:39]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 2024253-Iodobenzamide

Product 1

HCID 682830043-((Trimethylsilyl)ethynyl)benzamide

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-iodobenzamide (I29) (1.65 g, 6.66 mmol), Cu(I)I (127 mg, 0.666 mmol) and triphenylphosphine (524 mg, 2.00 mmol) in THF (100 mL) and triethylamine (4.64 mL, 33.3 mmol) was sonicated for 10 minutes under a nitrogen atmosphere. PdCl2(PPh3)2 (642 mg, 0.67 mmol) and TMS acetylene (1.88 mL, 13.3 mmol) were then added and the reaction stirred at room temperature for 3 days. The volatiles were evaporated in vacuo and the residue chromatographed on silica gel (0-50% ethyl acetate/petroleum benzine 40-60° C.) to give the title compound (I30) (1.53 g); 1H NMR (400 MHz, CDCl3) δ 7.78 (t, J=1.5 Hz, 1H), 7.67 (ddd, J=7.8, 1.8, 1.2 Hz, 1H), 7.53-7.48 (m, 1H), 7.29 (td, J=7.8, 0.5 Hz, 1H), 0.15 (s, 9H).

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customthe residue chromatographed on silica gel (0-50% ethyl acetate/petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-fa473d889e3b4152beb04e3db298ac90
Source dataset
uspto-grants-2015_11
Patent number
US09174946B2

Reaction notes

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