Trimethylsilylacetylene → 5-Methyl-2-trimethylsilanyl-furo[3,2-b]pyridine

HRID 1175732Notes

Reaction equation

HRID 1175732 reaction equation
I[C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12]>C(N(CC)CC)C>[CH3:8][C:6]1[N:7]=[C:2]2[CH:15]=[C:14]([Si:11]([CH3:13])([CH3:12])[CH3:10])[O:9][C:3]2=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 899572-Iodo-6-methylpyridin-3-ol

Product 1

HCID 114356745-Methyl-2-trimethylsilanyl-furo[3,2-b]pyridineYield 81%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a degassed solution of 6-iodo-2-picolin-5-ol (855 mg; 3.64 mmol; 1.00 eq.) in triethylamine (20.00 mL) were added (trimethylsilyl)acetylene (1 g; 10.19 mmol; 2.80 eq.), cuprous iodide (90.07 mg; 0.47 mmol; 0.13 eq.) and dichlorobis(triphenyl phosphine) palladium(II) (229.82 mg; 0.33 mmol; 0.09 eq.). The solution was heated under reflux. After 3 h, the reaction was complete, and allowed to cool down to rt. The solution was filtered over celite (washed with AcOEt and MeOH). The solvents were removed. AcOEt and water were added and the combined organic layers were dried over magnesium sulfate, filtered and concentrated to give the expected compound. The crude was purified by short flash chromatography using cyclohexane then AcOEt/Cyclohexane 20/80 to afford 603 mg of the desired compound as a solid (Intermediate 5.1). Amount: 603 mg; Yield: 81%; Formula: C11H15NOSi; HPLC Purity: 93.14%; HPLC H2O TFA 0.1%-ACN TFA 0.05%): Rt (min); Area %=2.17 min; 93.14%; 1H NMR (CDCl3) δ 7.65 (d, 1H, J=8.5 Hz), 7.10 (s, 1H), 7.06 (d, 1H, J=8.5 Hz), 2.67 (s, 3H), 0.36 (s, 9H); LC-MS: M/Z ESI: Rt (min) 1.89 min, 206.06 (M+1).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux
  3. filtrationThe solution was filtered over celite (washed with AcOEt and MeOH)
  4. customThe solvents were removed
  5. additionAcOEt and water were added
  6. dry with materialthe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-81574d825c544ef7b492b47896c8e998
Source dataset
uspto-grants-2010_11
Patent number
US07842698B2

Reaction notes

Loading…