Triethylamine → HCID 67233834, compound

HRID 2368751Notes

Reaction equation

HRID 2368751 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[C:9]([OH:18])=[C:10]2[CH:17]=[CH:16][S:15][C:11]2=[C:12](Br)[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[C:19]([Si:21]([CH3:24])([CH3:23])[CH3:22])#[CH:20].C(N(CC)CC)C>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.O>[CH2:1]([O:5][C:6]([C:8]1[C:9]([OH:18])=[C:10]2[CH:17]=[CH:16][S:15][C:11]2=[C:12]([C:20]#[C:19][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 86607517HCID 86607517, compound

Product 1

HCID 67233834HCID 67233834, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-bromo-4-hydroxy-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester (example 43 a, 165 mg, 0.5 mmol), ethynyl-trimethyl-silane (87 μl, 0.6 mmol), dichlorobis(triphenylphosphine)palladium(II) (11 mg, 0.015 mmol), CuI (5 mg, 0.025 mmol), and triethylamine (1.5 ml) was heated in a microwave oven at 100° C. with stirring for 15 min. After cooling to ambient temperature water (20 ml) was added and the mixture was extracted with diethylether (1×30 ml). The organic phase was dried over MgSO4. Then silica gel was added and the mixture concentrated in vacuo. The residue was added on top of a short column filled with silica gel. Elution with ethyl acetate:hexanes=9:1 and in vacuo concentration gave the title compound as a dark oil (75 mg); MS-(+)-ion: MS-(+)-ion: M+1=348.4.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with diethylether (1×30 ml)
  3. dry with materialThe organic phase was dried over MgSO4
  4. additionThen silica gel was added
  5. concentrationthe mixture concentrated in vacuo
  6. additionThe residue was added on top of a short column
  7. additionfilled with silica gel
  8. washElution with ethyl acetate
  9. concentrationhexanes=9:1 and in vacuo concentration

Sources & evidence

ORD record
ord-90f88b7d56b14c259642bf929fa51cf7
Source dataset
uspto-grants-2014_04
Patent number
US08703795B2

Reaction notes

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