Sodium Bicarbonate → HCID 10236611, compound

HRID 586238

Reaction equation

HRID 586238 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][C:3]=1[O:17][CH3:18].Br[C:20]1[N:24]2[N:25]=[CH:26][C:27]([C:29]([F:32])([F:31])[F:30])=[N:28][C:23]2=[N:22][CH:21]=1.C([O-])(O)=O.[Na+]>COCCOC.C(OCC)(=O)C.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>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:20]2[N:24]3[N:25]=[CH:26][C:27]([C:29]([F:30])([F:31])[F:32])=[N:28][C:23]3=[N:22][CH:21]=2)=[CH:4][C:3]=1[O:17][CH3:18]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 11601416HCID 11601416, compoundHCID 222853052-(4-Fluoro-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 10236611HCID 10236611, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-(4-fluoro-3-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (0.637 g, 2.528 mmol), 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.5 g, 1.873 mmol) and saturated aqueous NaHCO3 (10 ml) in 1,2-dimethoxyethane (25 ml) was degassed by evacuation and refilling with nitrogen three times. Tetrakis(triphenylphosphine)palladium(0) (0.169 g, 0.078 mmol) was added and the mixture was stirred under nitrogen at 95° C. for 17 h. After allowing to cool to ambient temperature, the mixture was diluted with ethyl acetate then filtered through glass fibre paper. The combined filtrates were partitioned between water (100 ml) and ethyl acetate (100 ml). The organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 25% EtOAc/isohexane), to give 275 mg (47%) of the title compound: 1H NMR (360 MHz, CDCl3) δ 4.00 (3H, s), 7.26 (1H, dd, J 10.9, 8.4 Hz), 7.61-7.64 (1H, m), 7.76 (1H, dd, J 2.1, 8.1 Hz), 8.58 (1H, s), 8.81 (1H, s).

Workup

  1. customwas degassed by evacuation and refilling with nitrogen three times
  2. temperatureto cool to ambient temperature
  3. filtrationthen filtered through glass fibre paper
  4. customThe combined filtrates were partitioned between water (100 ml) and ethyl acetate (100 ml)
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography (silica gel, 25% EtOAc/isohexane)

Sources & evidence

ORD record
ord-03bbaca8427945e7b5ae4c7d0ecb60fb
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Linked notes

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