Potassium Carbonate → HCID 44478092, compound

HRID 17107Notes

Reaction equation

HRID 17107 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si]([C:11]#[C:12][C:13]1[N:18]=[C:17]([NH:19][C:20](=[O:22])[CH3:21])[CH:16]=[CH:15][CH:14]=1)(C)C>CO>[C:12]([C:13]1[N:18]=[C:17]([NH:19][C:20](=[O:22])[CH3:21])[CH:16]=[CH:15][CH:14]=1)#[CH:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 44478150N-(6-(2-(Trimethylsilyl)ethynyl)-2-pyridinyl)acetamide

Product 1

HCID 44478092HCID 44478092, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Anhydrous potassium carbonate (110 mg, 0.8 mmoles) was added to a solution of N-(6-((trimethylsilyl)ethynyl)pyridine-2-yl)acetamide (1.86 g, 8 mmol) in 20 ml anhydrous methanol. The reaction mixture was stirred at room temperature for fifteen minutes then filtered. The filtrate was concentrated in vacuo. The crude product mixture was chromatographed on Silica Gel (230-400 Mesh) eluting with 2.5% MeOH/98% CH2Cl2 to yield A436.1 as an off-white solid. (770 mg, 60% yield). M+H+=218.20 1H NMR (400 MHz) MEOD δ 8.13 (m, 1H), 7.75 (m, 1H), 7.27 (m, 1H), 3.65 (s, 1H), 2.18 (s, 3H).

Workup

  1. filtrationthen filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe crude product mixture was chromatographed on Silica Gel (230-400 Mesh)
  4. washeluting with 2.5% MeOH/98% CH2Cl2
  5. customto yield A436.1 as an off-white solid

Sources & evidence

ORD record
ord-21d8f692ec4a4409aa8b70bdc10a11a2
Source dataset
uspto-grants-2010_06
Patent number
US07737279B2

Reaction notes

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