Sodium Carbonate → HCID 68006677, compound

HRID 2401771Notes

Reaction equation

HRID 2401771 reaction equation
[CH:1]([B-](F)(F)F)=[CH2:2].[K+].O1CCOCC1.Br[C:15]1[N:16]=[C:17]([C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)[S:18][C:19]=1[C:20]1[N:24]=[CH:23][N:22]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[N:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O.O>[CH3:30][Si:29]([CH3:32])([CH3:31])[CH2:28][CH2:27][O:26][CH2:25][N:22]1[CH:23]=[N:24][C:20]([C:19]2[S:18][C:17]([C:33]3[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=3)=[N:16][C:15]=2[CH:1]=[CH2:2])=[N:21]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 23679353Potassium vinyltrifluoroborateHCID 66749351HCID 66749351, compound

Product 1

HCID 68006677HCID 68006677, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Into a sealed tube was added potassium vinyltrifluoroborate (1.34 g, 10.0 mmol), 1,4-dioxane (21.0 mL, 269 mmol), 4-[4-bromo-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]pyridine (2.0 g, 4.6 mmol) and 2 M sodium carbonate in water (9.10 mL, 18.2 mmol). The reaction was degassed with nitrogen for 15 min then tetrakis(triphenylphosphine)palladium(0) (527 mg, 0.456 mmol) was added. The tube was sealed and the reaction was heated in an oil bath at 110° C. with stirring overnight. The reaction solution was cooled to room temperature, water (10 mL) and EtOAc (10 mL) were added, and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The obtained residue was purified by column chromatography (SiO2, elution with 0-10% MeOH in DCM) to give the title compound as a yellow solid (1.34 g 81%). LCMS: (FA) ES+ , 386. 1H NMR (400 MHz, d6-DMSO) δ: 8.92 (s, 1H), δ 8.74-8.76 (dd, J=1.75 Hz, J=1.5 Hz 2H), 7.96-7.98 (dd, J=1.75 Hz, 2H), 6.34-6.40 (dd, J=2.3 Hz, 12H), 5.62-5.65 (dd, J=2.3 Hz, 1H), 5.60 (s, br, 2H), 3.63-3.68 (m, 2H), 0.86-0.90 (m, 2H), −0.04 (s, 9H).

Workup

  1. customThe reaction was degassed with nitrogen for 15 min
  2. customThe tube was sealed
  3. temperatureThe reaction solution was cooled to room temperature
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by column chromatography (SiO2, elution with 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-86465bd67f984f90bb28b2f1d34a34b9
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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