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Triethylamine → 5-((Trimethylsilyl)ethynyl)picolinaldehyde

HRID 2281796
Notes
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Reaction equation

HRID 2281796 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[Si:10]([C:14]#[CH:15])([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C.C(OCC)(=O)C>C1COCC1.[Cu](I)I.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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:11][Si:10]([C:14]#[C:15][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1)([CH3:13])[CH3:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 114014485-((Trimethylsilyl)ethynyl)picolinaldehydeYield 95%

Reagents, catalysts & solvents 4

HCID 11776
Triphenylphosphine
Catalyst
HCID 83717Copper iodideCatalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-bromopicolinaldehyde (1 g, 5.3 mmol), TMS-acetylene (1.04 g, 10.6 mmol) and triethylamine (4 mL) in THF (10 mL) was purged with argon for 10 min. Copper iodide (76 mg, 0.4 mmol), Pd(PPh3)2Cl2 (141 mg, 0.4 mmol) and triphenylphosphine (0.1 g, 0.4 mmol) was added and the mixture was heated to 100° C. under microwave irradiation for 10 min. Ethyl acetate (200 mL) was added at the solution was washed with water (2×25 mL), dried over MgSO4 and concentrated to dryness. The residue was filtered through silica gel with CH2Cl2 to give the title compound as a yellow oil (1 g, 95%). 1H NMR (400 MHz, CDCl3) δ 10.08 (s, 1H), 8.82 (s, 1H), 7.91 (s, 2H), 0.29 (s, 9H).

Workup

  1. washwas washed with water (2×25 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to dryness
  4. filtrationThe residue was filtered through silica gel with CH2Cl2

Sources & evidence

ORD record
ord-87484da103504ff88bb378034e384f8f
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09139563B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes