Thieno(2,3-c)pyridine → HCID 10740978, compound

HRID 2173021Notes

Reaction equation

HRID 2173021 reaction equation
[S:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C([Li])CCC.[CH2:15]([Sn:19]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])Cl)[CH2:16][CH2:17][CH3:18].C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:25]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:21][CH2:22][CH2:23][CH3:24])[C:2]1[S:1][C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1)[CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 9224Thieno(2,3-c)pyridineHCID 15096Tributyltin ChlorideHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

Product 1

HCID 10740978HCID 10740978, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a cold (−78° C.) solution of thieno[2,3-c]pyridine (524 mg, 3.88 mmol) in anhydrous THF (50 mL) was added n-butyllithium (2.66 mL, 4.26 mmol) dropwise. The mixture was stirred for 60 minutes at −78° C. A solution of tributylchlorostannane (1.254 mL, 4.65 mmol) in anhydrous THF (10 mL) was added, and the reaction mixture was stirred for 30 minutes at −78° C. The solution was allowed to warm to room temperature over a period of 2 to 3 hours. Saturated aqueous sodium bicarbonate was added. The aqueous phase was extracted with diethyl ether (3×200 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo. The crude product was purified by silica gel column chromatography, eluting with a gradient of 10-50% EtOAc and hexane over a period of 60 minutes. The desired fractions were collected to give the title compound as a clear oil (1.1 g, 67%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.86 (t, J=7.32 Hz, 9H), 1.08-1.38 (m, 12H), 1.45-1.71 (m, 6H), 7.59 (s, 1H), 7.76-7.93 (m, 1H), 8.41 (s, 1H), 9.23 (s, 1H).

Workup

  1. stirringthe reaction mixture was stirred for 30 minutes at −78° C
  2. temperatureto warm to room temperature over a period of 2 to 3 hours
  3. extractionThe aqueous phase was extracted with diethyl ether (3×200 mL)
  4. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude product was purified by silica gel column chromatography
  8. washeluting with a gradient of 10-50% EtOAc and hexane over a period of 60 minutes
  9. customThe desired fractions were collected

Sources & evidence

ORD record
ord-0748c4be3b6e45ed8a139c7e88ed301c
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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