Triethylamine → HCID 67167639, compound

HRID 874709Notes

Reaction equation

HRID 874709 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8](I)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Si:12]([C:16]#[CH:17])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>[Cu](I)I>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([C:17]#[C:16][Si:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 72911Benzoic acid, 2-amino-5-iodo-

Product 1

HCID 67167639HCID 67167639, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

2-amino-5-iodobenzoic acid (500 mg, 1.9 mmol, 1 eq.) was dissolved in nitrogen-degassed THF (10 mL) at room temperature. TMS-acetylene (0.34 mL, 2.5 mmol, 1.3 eq.), nitrogen-degassed triethylamine (0.8 mL, 5.7 mmol, 3 eq.), dichloro-bis(triphenylphosphine)palladium(II) (267 mg, 0.4 mmol, 0.2 eq.), and copper iodide (145 mg, 0.8 mmol, 0.4 eq.) were added, in order, to the reaction in the dark. The reaction was then stirred at room temperature for 20 minutes. The solvent was evaporated, and the residue was purified on silica column (DCM/MeOH, 39:1→19:1) to result in 315 mg (71%) of the title compound as a dark orange solid. 1H NMR (500 MHz, CDCl3) δ 8.07 (d, J=1.7, 1H, Ar—H), 7.37 (dd, J=1.8, 8.6, 1H, Ar—H), 6.57 (d, J=8.6, 1H, Ar—H), 0.22 (s, 9H, SiC3H9). 13C NMR (126 MHz, CDCl3) δ 173.11 (COOH), 151.15 (C—Ar), 138.41 (C—Ar), 136.64 (C—Ar), 116.94 (C—Ar), 111.06 (C—Ar), 109.23 (C—Ar), 104.98 (CSi(CH3)3), 92.02 (CCSi(CH3)3), 0.29 (Si(CH3)3). Exact Mass, 233.09. 231.7418 [M−H]−, 233.7569 [M+H]+.

Workup

  1. customdegassed THF (10 mL) at room temperature
  2. additionwere added, in order, to the reaction in the dark
  3. customThe solvent was evaporated
  4. customthe residue was purified on silica column (DCM/MeOH, 39:1→19:1)

Sources & evidence

ORD record
ord-6ba57e6cc44245e5a63f3342a77f2561
Source dataset
uspto-grants-2015_03
Patent number
US08980926B2

Reaction notes

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