Potassium Carbonate → HCID 59843096, compound

HRID 1878732Notes

Reaction equation

HRID 1878732 reaction equation
[F:1][C:2]1[C:7]([CH2:8][CH2:9][OH:10])=[CH:6][C:5](I)=[CH:4][N:3]=1.[CH3:12][C:13]1[CH:14]=[C:15](B(O)O)[S:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>[Pd].O1CCOCC1>[F:1][C:2]1[C:7]([CH2:8][CH2:9][OH:10])=[CH:6][C:5]([C:15]2[S:16][CH:17]=[C:13]([CH3:12])[CH:14]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343734-Methylthiophene-2-boronic acidHCID 59843011HCID 59843011, compound

Product 1

HCID 59843096HCID 59843096, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a microwave tube was added 2-(2-fluoro-5-iodopyridin-3-yl)ethanol (0.09 g, 0.3 mmol), 4-methylthiophen-2-ylboronic acid (0.2 g, 1 mmol), palladium fibrecatalyst (0.010 mg, 10% wt), potassium carbonate (2 M, 0.3 mL, 0.7 mmol), and dioxane (3 mL). The vial was sealed and placed into CEM microwave for 20 min. at 150° C., with 80 Watts of power via Powermax. The reaction mixture was partitioned between water/CH2Cl2. The aqueous layer was extracted with CH2Cl2 and the combined organic layers were dried over MgSO4 and concentrated. The crude product was purified using SiO2 chromatography with hexane:acetone (90%:10%) to afford the product as colorless liquid (65 mg). MS (ESI pos. ion) m/z (MH+): 238.3. Calc'd exact mass for C12H12FNOS: 237.1. 1H NMR (300 MHz, Chloroform-d) δ ppm 1.54-1.64 (m, 1 H) 2.30 (s, 3 H) 2.94 (t, J=6.36 Hz, 2 H) 3.95 (q, J=6.24 Hz, 2 H) 6.92 (s, 1 H) 7.11 (s, 1 H) 7.84 (d, J=9.06 Hz, 1 H) 8.27 (s, 1 H).

Workup

  1. customThe vial was sealed
  2. customThe reaction mixture was partitioned between water/CH2Cl2
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-c8cddb67ff0d4304a7b7d4c1d094f713
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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