Triethylamine → HCID 86607518, compound

HRID 1465968Notes

Reaction equation

HRID 1465968 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:13]=[C:12](Br)[C:11]2[CH:15]=[CH:16][S:17][C:10]=2[C:9]=1[OH:18])=[O:7])[CH2:2][CH2:3][CH3:4].[C:19]([Si](C)(C)C)#[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[N:13]=[C:12]([C:19]#[CH:20])[C:11]2[CH:15]=[CH:16][S:17][C:10]=2[C:9]=1[OH:18])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 86607519HCID 86607519, compound

Product 1

HCID 86607518HCID 86607518, compoundYield 21.8%

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 4-bromo-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid butyl ester (example 44a, 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 (30 mg); MS-(+)-ion: MS-(+)-ion: M+1=275.9.

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-3009b11375604360b4195aa22b6a68af
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

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