Diisopropylethylamine → HCID 11335299, compound

HRID 1785007Notes

Reaction equation

HRID 1785007 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][Si:11]([CH3:16])([CH3:15])[CH2:12][C:13]#[CH:14].[CH2:17]([C:19]1[C:20]([C:27]([O:29][CH3:30])=[O:28])=[C:21]([CH:25]=[O:26])[NH:22][C:23]=1I)[CH3:18]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I.O1CCOCC1>[CH2:17]([C:19]1[C:20]([C:27]([O:29][CH3:30])=[O:28])=[C:21]([CH:25]=[O:26])[NH:22][C:23]=1[C:14]#[C:13][CH2:12][Si:11]([CH3:16])([CH3:15])[CH3:10])[CH3:18]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 83378Trimethyl-2-propynylsilaneHCID 11278208Methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate

Product 1

HCID 11335299HCID 11335299, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate was obtained following the procedures described in Example 3. Pd(Pt-Bu3)4 (18.4 mg, 0.040 mmol), Pd2(dba)3 (16.5 mg, 0.020 mmol), and CuI (4.6 mg, 0.020 mmol) were combined in a dry flask under N2 prior to evacuating the flask and refilling with argon. After the flask was charged with dioxane (4.0 mL), i-Pr2NEt (0.0675 mL, 0.48 mmol), trimethyl(prop-2-ynyl)silane (90.0 mg, 0.80 mmol), and methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate (123.0 mg, 0.40 mmol) were added sequentially. The reaction was stirred overnight at 80° C. After the reaction was cooled to ambient temperature, it was filtered through a plug of silica gel and concentrated in vacuo. The resultant residue was dissolved in acetonitrile and purified by reverse phase HPLC. Proton NMR for the product was consistent with the title compound. 1H NMR (500 MHz, CDCl3) δ 10.04 (s, 1H); 3.90 (s, 3H); 2.78 (q, J=7.5 Hz, 2H); 1.77 (s, 2H); 1.16 (t, J=7.5 Hz, 3H); 0.17 (s, 9H). HRMS (ES) exact mass calculated C15H22NO3Si (M+H): 292.1364. Found 292.1364

Workup

  1. customto evacuating the flask
  2. additionwere added sequentially
  3. temperatureAfter the reaction was cooled to ambient temperature
  4. filtrationit was filtered through a plug of silica gel
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resultant residue was dissolved in acetonitrile
  7. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-5f4d8741ddbd431a8594357909836278
Source dataset
uspto-grants-2009_03
Patent number
US07504429B2

Reaction notes

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